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Journal articles on the topic 'Relative stereochemistry'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Zheng, Wanjun, John A. DeMattei, Jiang-Ping Wu, et al. "Complete Relative Stereochemistry of Maitotoxin." Journal of the American Chemical Society 118, no. 34 (1996): 7946–68. http://dx.doi.org/10.1021/ja961230+.

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2

Smith, Amos B., Joseph Barbosa, Nobuo Hosokawa, Hiroshi Naganawa, and Tomio Takeuchi. "(+)-Thiazinotrienomycin E: Relative and absolute stereochemistry." Tetrahedron Letters 39, no. 19 (1998): 2891–94. http://dx.doi.org/10.1016/s0040-4039(98)00426-2.

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3

Pirrung, Michael C., Yong Rok Lee, Andrew T. Morehead, and Andrew T. McPhail. "Revised Relative and Absolute Stereochemistry of (+)-Purpurin." Journal of Natural Products 61, no. 1 (1998): 89–91. http://dx.doi.org/10.1021/np970366y.

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4

Dormer, Peter G., Amos B. Smith, Shinji Funayama, and Satoshi Omura. "Furaquinocins A-G: relative and absolute stereochemistry." Tetrahedron Letters 33, no. 13 (1992): 1717–20. http://dx.doi.org/10.1016/s0040-4039(00)91714-3.

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5

Burns, CJ, M. Gill, and A. Gimenez. "Pigments of Fungi. XXIV. New Trihydroxylated Tetrahydroanthraquinones From an Australian Fungus Belonging to the Genus Dermocybe." Australian Journal of Chemistry 44, no. 12 (1991): 1729. http://dx.doi.org/10.1071/ch9911729.

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The pigments (9)-(11), the first trihydroxylated tetrahydroanthraquinones from Basidiomycetes, are isolated from an Australian toadstool belonging to the genus Dermocybe and the structure and relative stereochemistry of each one is established by spectroscopy. The absolute stereochemistry of each pigment is determined by synthesis from dihydroxylated tetrahydroanthraquinones of known absolute configuration.

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6

Bowden, BF, JC Coll, LM Engelhardt, et al. "Studies of Australian Soft Corals .XXXVII. The Structure Determination of 2 Cembranolide Diterpenes From Soft Corals of the Genus Efflatounaria (Coelenterata, Octocorallia, Alcyonacea)." Australian Journal of Chemistry 39, no. 1 (1986): 123. http://dx.doi.org/10.1071/ch9860123.

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Two isomeric 7,8-epoxycembra-3,11,15-trien-16,2-olides have been isolated from different species of the soft coral genus Efflatounaria. The structure of each was deduced spectroscopically , and the relative stereochemistry of one was determined by X-ray crystallography. The absolute stereochemistry of each cembranolide was obtained by chemical correlation with known compounds.

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7

Bali, DKL, V. Liokas, MJ Garson, and DJ Faulkner. "Structural and Stereochemical Studies on Brominated Meroterpenoids From the Dictyoceratid Sponge Cacospongia sp." Australian Journal of Chemistry 43, no. 12 (1990): 2009. http://dx.doi.org/10.1071/ch9902009.

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The structures of seven minor metabolites, (5)-(11), from the encrusting sponge Cacospongia sp. Were deduced by 1H, 13C and mass spectrometric data. Compounds (5)-(7) are hydroxy derivatives of the previously isolated tribromocacoxanthene (1); their relative stereochemistry was determined from 1H-1H coupling information. Compounds (8)-(11) represent an alternative cyclization mode of a cyclocymopol-related precursor (15) and possess a spiro-fused bicyclic ring system; the relative stereochemistry of (8)-(10) was deduced by 1H n.O.e. difference spectroscopy. The biological role of brominated me

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8

Wang, Xiaojuan, and Mark T. Hamann. "Integrated X-Ray, NMR, ECD, and Computational Approaches to Assign the Stereochemistry of Nortriterpenoids." Natural Product Communications 14, no. 5 (2019): 1934578X1984931. http://dx.doi.org/10.1177/1934578x19849311.

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Highly oxygenated nortriterpenoids are the principle bioactive chemical constituents isolated from plants of the genera Schisandra and Kadsura. The stereochemistry of these molecules remains a highly challenging problem to solve. To establish the stereochemistry and develop a general nuclear magnetic resonance-electric circular dichroism-computational approach to solve these complex metabolites, we reviewed the published methods to solve the stereochemistry of these triterpenoids. A key goal of this review is to provide a protocol to solve the problems hampering the assignment of the relative

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9

Bisio, Angela, Bruno Pagano, Alessia Romussi, et al. "Relative Stereochemistry of a Diterpene from Salvia cinnabarina." Molecules 12, no. 10 (2007): 2279–87. http://dx.doi.org/10.3390/12102279.

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10

Smith, Amos B., John L. Wood, and Satoshi Ōmura. "(+)-Mycotrienins I and II: Relative and Absolute Stereochemistry." Tetrahedron Letters 32, no. 7 (1991): 841–42. http://dx.doi.org/10.1016/s0040-4039(00)92099-9.

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11

SMITH, A. B. III, and J. BARBOSA. "ChemInform Abstract: (+)-Thiazinotrienomycin E: Relative and Absolute Stereochemistry." ChemInform 29, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199830276.

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12

Pyne, SG, B. Dikic, BW Skelton, and AH White. "Chiral Sulfur Compounds. XV. Diastereoselective Additions of Lithiated S-Benzyl-N-t-butyldiphenylsilyl-S-methyl-sulfoximine to Imines and Aldehydes." Australian Journal of Chemistry 45, no. 5 (1992): 807. http://dx.doi.org/10.1071/ch9920807.

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The lithium salt of racemic S-benzyl-N-t- butyldiphenylsilyl-S-methylsulfoximine (2) undergoes 1,2-addition to imines that have been activated by precomplexation with boron trifluoride diethyl etherate (BF3.Et2O), and aldehydes , with high diastereoselectivity. The relative lS*,2S.*,S*s stereochemistry of the major diastereomeric adducts of (2) and EtCH = NPh and PriCH = NPh , and the relative lS *,2S*,S*s stereochemistry of the major diastereomeric adduct of (2) and propanal were unequivocally determined by single-crystal X-ray structure analysis. An open transition state has been proposed to

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13

Chen, Jie, Panduka Koswatta, J. Robb DeBergh, et al. "Structure elucidation of nigricanoside A through enantioselective total synthesis." Chemical Science 6, no. 5 (2015): 2932–37. http://dx.doi.org/10.1039/c5sc00281h.

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14

Soloshonok, Vadim A., and Donna J. Nelson. "Alkene selenenylation: A comprehensive analysis of relative reactivities, stereochemistry and asymmetric induction, and their comparisons with sulfenylation." Beilstein Journal of Organic Chemistry 7 (June 3, 2011): 744–58. http://dx.doi.org/10.3762/bjoc.7.85.

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A broad perspective of various factors influencing alkene selenenylation has been developed by concurrent detailed analysis of key experimental and theoretical data, such as asymmetric induction, stereochemistry, relative reactivities, and comparison with that of alkene sulfenylation. Alkyl group branching α to the double bond was shown to have the greatest effect on alkene reactivity and the stereochemical outcome of corresponding addition reactions. This is in sharp contrast with other additions to alkenes, which depend more on the degree of substitution on C=C or upon substituent electronic

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15

Hanif, Novriyandi, Anggia Murni, Marie Yamauchi, Masahiro Higashi, and Junichi Tanaka. "A New Trinor-guaiane Sesquiterpene from an Indonesian Soft Coral Anthelia sp." Natural Product Communications 10, no. 11 (2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001124.

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A new trinor-guaiane sesquiterpene has been isolated from an Indonesian soft coral Anthelia sp. The planar structure, possessing an octahydroazulene skeleton, and relative stereochemistry were established by analyzing 1D and 2D NMR data, including NOE experiments. Its absolute stereochemistry was elucidated to be 1 S, 4 S, 7 R, and 10 R by comparing observed and calculated optical rotation values. The new compound showed weak cytotoxicity against NBT-T2 cells.

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16

Westphal, Klaus Ringsborg, Manuela Ilse Helga Werner, Katrine Amalie Hamborg Nielsen, et al. "Characterization of Eight Novel Spiroleptosphols from Fusarium avenaceum." Molecules 24, no. 19 (2019): 3498. http://dx.doi.org/10.3390/molecules24193498.

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Chemical analyses of Fusarium avenaceum grown on banana medium resulted in eight novel spiroleptosphols, T1, T2 and U–Z (1–8). The structures were elucidated by a combination of high-resolution mass spectrometric data and 1- and 2-D NMR experiments. The relative stereochemistry was assigned by 1H coupling and NOESY/ROESY experiments. Absolute stereochemistry established for 7 by vibrational circular dichroism was found analogous to that of the putative polyketide spiroleptosphol from Leptosphaeria doliolum.

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17

Blanchfield, JT, DJ Brecknell, IM Brereton, MJ Garson, and DD Jones. "Caloundrin B and Funiculatin A: New Polypropionates From Siphonariid Limpets." Australian Journal of Chemistry 47, no. 12 (1994): 2255. http://dx.doi.org/10.1071/ch9942255.

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Two new polypropionates, caloundrin B (11), systematic name (1″R,2R,3″R,4R,5S,5″R,6S,-7″R,8″S,9″S,10″R)-2-(6′-ethyl-3′,5′-dimethyl-4′-oxopyran-2′-yl)-6-(5″-ethyl-7″-hydroxy-8″,9″,10″-trimethyl-2″,4″,6″-trioxatricyclo[3.3.1.13,7]dec-3″-yl)-5-hydroxy-4-methylheptan-3-one, and funiculatin A (12), systematic name (2ξ,1′S,4R,5′S,6′S)-2-(1′-ethyl-4′,6′,8′-trimethyl-2𔈀,9′-dioxabicyclo[3.3.1]nona-3′,7′-dien-3′-yl)-4,6-dimethylnon-6-en-3-one, have been isolated from Siphonaria zelandica and S. funiculata respectively. The structures of the new compounds were deduced by two-dimensional n.m.r. spectrosco

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18

Polborn, K., W. Steglich, J. D. Connolly, and S. Huneck. "Structure of the Macrocyclic Bis-lactone Lepranthin from the Lichen Arthonia impolita; an X-Ray Analysis." Zeitschrift für Naturforschung B 50, no. 7 (1995): 1111–14. http://dx.doi.org/10.1515/znb-1995-0723.

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19

Mandal, Dipak K. "Dynamic Stereochemistry: A Simple Approach To Delineating Relative Configuration." Journal of Chemical Education 84, no. 2 (2007): 274. http://dx.doi.org/10.1021/ed084p274.

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20

Smith, Amos B., John L. Wood, Weichyun Wong, et al. "(+)-Trienomycins A, B, and C: relative and absolute stereochemistry." Journal of the American Chemical Society 112, no. 20 (1990): 7425–26. http://dx.doi.org/10.1021/ja00176a070.

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21

Harmange, Jean-Christophe, Craig D. Boyle, and Yoshito Kishi. "Relative and absolute stereochemistry of the fumonisin B2 backbone." Tetrahedron Letters 35, no. 37 (1994): 6819–22. http://dx.doi.org/10.1016/0040-4039(94)85013-5.

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22

Jervis, Peter J., and Liam R. Cox. "Total Synthesis and Proof of Relative Stereochemistry of (−)-Aureonitol." Journal of Organic Chemistry 73, no. 19 (2008): 7616–24. http://dx.doi.org/10.1021/jo801338t.

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23

Han, Feipeng, Yian Guo, and Tao Ye. "Total synthesis of antiallergic bicyclic peptide seongsanamide A." Organic Chemistry Frontiers 7, no. 13 (2020): 1658–62. http://dx.doi.org/10.1039/d0qo00531b.

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24

Bourguignon, Jean, Gilles Le Nard, and Guy Queguiner. "Synthèse d'aryl nitronorbornènes par cycloaddition de Diels–Alder entre les aryl-nitroéthylènes et le cyclopentadiène. Justification de la stéréochimie et de la réactivité relative observées par la méthode CNDO/II. Obtention d'aryl aminonorbornènes." Canadian Journal of Chemistry 63, no. 9 (1985): 2354–61. http://dx.doi.org/10.1139/v85-390.

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Syntheses of numerous 2-aryl nitroethylenes (nitrostyrenes) have been optimized. The nitrostyrenes have been reacted with cyclopentadiene in Diels–Alder cycloadditions and the 3-aryl 2-nitronorbornenes obtained have been reduced into 3-aryl 2-aminonorbornenes. These compounds are potentially dopaminergic molecules. The stereochemistry of the adducts obtained in the Diels–Alder reaction has been determined by 1H nmr. The stereochemistry and the relative reactivity of the nitrostyrenes versus cyclopentadiene have been confirmed by theoretical calculations based on the CNDO/II method.

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25

Parker, Samuel, David Watkin, Benjamin Mayes, Richard Storer, Sarah Jenkinson, and George Fleet. "2-Deoxy-2-fluoro-2-C-methyl-D-ribono-1,4-lactone (fluoromethylrib)." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (2006): o1208—o1210. http://dx.doi.org/10.1107/s1600536806006337.

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26

Coll, JC, BW Skelton, AH White, and AD Wright. "Tropical Marine Algae. II. The Structure Determination of New Halogenated Monoterpenes From Plocamium hamatum (Rhodophyta, Gigartinales, Plocamiaceae)." Australian Journal of Chemistry 41, no. 11 (1988): 1743. http://dx.doi.org/10.1071/ch9881743.

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The structure determinations of new halogenated monoterpenes, isolated from collections of Plocamium hamatum J. Agardh , are reported. One collection of P. hamatum afforded (1R*,2R*,4S*,5R*,1′E)-1,2,4- trichloro-5-(2′-chloroethenyl)-1,5-dimethylcyclohexane (1) whose relative stereochemistry was determined by X-ray crystallography. Extensive use of two-dimensional carbon-hydrogen correlation experiments enabled unambiguous assignments of proton and carbon resonances to be made for this new compound. Complete carbon assignments for the related metabolite mertensene (2) are reported. A second col

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27

Yabe, Ryota, Yusuke Ebe та Takahiro Nishimura. "Iridium-catalyzed stereoselective [3+2] annulation of α-oxocarboxylic acids with 1,3-dienes". Chemical Communications 57, № 48 (2021): 5917–20. http://dx.doi.org/10.1039/d1cc02003j.

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The stereoselective annulation of α-oxocarboxylic acids with 1,3-dienes proceeded in the presence of a hydroxoiridium catalyst to give α-hydroxy-γ-lactones in good yields with high 3,5-trans relative stereochemistry.

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28

Grunwald, Alyssa L., Fabrice Berrué, David P. Overy, and Russell G. Kerr. "Isolation of iqalisetins A and B from a Tolypocladium sp. isolated from marine sediment from Frobisher Bay in Canada’s arctic." Canadian Journal of Chemistry 94, no. 4 (2016): 444–48. http://dx.doi.org/10.1139/cjc-2015-0439.

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Two new decalin-tetramic acid compounds, iqalisetin A (1) and iqalisetin B (2), were identified from a Tolypocladium sp. isolated from a marine sediment sample collected from Frobisher Bay, Nunavut, in Canada’s arctic. The structures of the new compounds were elucidated by NMR experiments. The relative stereochemistry of the decalin skeleton was determined by NOESY experiments and confirmed that 1 and 2 contained a trans-decalin ring system. The absolute stereochemistry of the tetramic acid was determined using Marfey’s method. Compounds 1 and 2 did not exhibit any significant antimicrobial or

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29

Carroll, AR, BF Bowden, JC Coll, DCR Hockless, BW Skelton, and AH White. "Studies of Australian Ascidians. IV. Mollamide, a Cytotoxic Cyclic Heptapeptide From the Compound Ascidian Didemnum molle." Australian Journal of Chemistry 47, no. 1 (1994): 61. http://dx.doi.org/10.1071/ch9940061.

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A new cytotoxic cyclic heptapeptide, mollamide, has been isolated from the compound ascidian Didemnum molle. The structure of mollamide was initially deduced from one-dimensional and two-dimensional n.m.r . experiments at 300 MHz. The structure was confirmed by an X-ray crystallographic study, which showed the relative stereochemistry of the cyclic peptide. Hydrolysis of mollamide , and characterization of the amino acids by derivatization with Nα -(5-fluoro-2,4-dinitrophenyl)-L- alaninamide (FDAA; Marfey's reagent) gave the absolute stereochemistry; all constituent amino acids were the L-isom

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30

Johnson, WMP, G. Holan, and KE Jarvis. "Synthesis and Relative Stereochemistry of 2-Monohalo Ddt Pyrethroid Structures - 2-Halo-1-(4′-Ethoxyphenyl)Cyclopropane-1-Methanols and Cyclopropane-1-Carboxylic Acids and Esters." Australian Journal of Chemistry 39, no. 2 (1986): 271. http://dx.doi.org/10.1071/ch9860271.

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This paper describes the essential features of the synthesis of a series of 2-monohalo DDT pyrethroid insecticides (8), as well as, the proof of the relative stereochemistry of substituents around the cyclopropane ring.

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31

Trendafilova, Antoaneta, Milka Todorova, Viktoriya Genova, et al. "New Pseudoguaiane Derivatives from Inula aschersoniana Janka var. aschersoniana." Natural Product Communications 9, no. 8 (2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900814.

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The aerial parts of Inula aschersoniana Janka var. aschersoniana afforded parthenolide, diepoxycostunolide, inusoniolide, chrysosplenol C and four new pseudoguaiane-type sesquiterpenoids. Their structures were determined using spectral methods and relative stereochemistry by NOESY correlations.

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32

Brook, Michael A. "The nomenclature of relative stereochemistry: Choosing between likes and preferences." Journal of Chemical Education 64, no. 3 (1987): 218. http://dx.doi.org/10.1021/ed064p218.

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33

Futagami, Shin, Yoriko Ohashi, Koreaki Imura, et al. "Total synthesis of ravidomycin: revision of absolute and relative stereochemistry." Tetrahedron Letters 41, no. 7 (2000): 1063–67. http://dx.doi.org/10.1016/s0040-4039(99)02235-2.

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34

Whitesell, James K., and Mark A. Minton. "Specification of relative stereochemistry in bridged bicyclic and spirobicyclic systems." Journal of Organic Chemistry 50, no. 4 (1985): 509–11. http://dx.doi.org/10.1021/jo00204a017.

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35

Dorta, Enrique, Ana R. Dı́az-Marrero, Mercedes Cueto, and José Darias. "On the relative stereochemistry of atomaric acid and related compounds." Tetrahedron 59, no. 12 (2003): 2059–62. http://dx.doi.org/10.1016/s0040-4020(03)00215-1.

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36

JOHNSON, JANICE H., D. W. PHILLIPSON, and ALICIA D. KAHLE. "The relative and absolute stereochemistry of the antifungal agent preussin." Journal of Antibiotics 42, no. 7 (1989): 1184–85. http://dx.doi.org/10.7164/antibiotics.42.1184.

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37

Kudryavtsev, Konstantin V., and Andrei V. Churakov. "4-[(1RS,5RS,7SR)-5-Methyl-2,4-dioxo-3,6-diazabicyclo[3.2.1]octan-7-yl]benzonitrile." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1718. http://dx.doi.org/10.1107/s1600536812020156.

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In the title compound, C14H13N3O2, the relative stereochemistry of the three stereogenic C atoms has been determined. In the crystal, N—H...O hydrogen bonds link the molecules into chains of inversion dimers running along the b axis.

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38

Lough, Alan J., Anna Allen, and William Tam. "Cyclodimerization product of benzooxanorbornadiene." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (2007): o1462—o1463. http://dx.doi.org/10.1107/s160053680700699x.

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The crystal structure determination of the title compound, (6aS*,6bR*,7R*,12R*,12aS*,12bS*)-7,12-epoxy-6a,6b,7,12,12a,12b-hexahydrodinaphtho[1,2-b;2,3-d]furan, C20H16O2, establishes the relative stereochemistry. There are four independent molecules in the asymmetric unit.

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39

Blanchfield, Joanne T., Sharon Chow, Paul V. Bernhardt, Colin H. L. Kennard, and William Kitching. "Concerning the Proposed Structure of (+)-Laurobtusol: Spectral Discrepancies with Synthetic, Racemic Stereoisomers." Australian Journal of Chemistry 57, no. 7 (2004): 673. http://dx.doi.org/10.1071/ch04047.

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Laurobtusol, a minor metabolite from Laurencia obtusa, had been assigned constitution 1 and relative stereochemistry, 2. However, several stereoisomers of this novel, cyclopropane-containing system 1 have now been synthesized and spectral correspondence between the synthesized isomers and laurobtusol is lacking.

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40

Edgeley, David S., Sarah F. Jenkinson, Gabriel Lenagh-Snow, Catherine Rutherford, George W. J. Fleet та Amber L. Thompson. "N-Benzyl-3,5-dideoxy-3,5-imino-1,2-O-isopropylidene-β-L-lyxofuranose". Acta Crystallographica Section E Structure Reports Online 68, № 8 (2012): o2410. http://dx.doi.org/10.1107/s1600536812030656.

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X-ray crystallography confirmed the formation, structure and relative stereochemistry of the title compound, C15H19NO3, which contains a sterically congested four-membered azetidine ring system. The absolute configuration was determined by the use of L-arabinose as the starting material.

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41

Carman, RM, KL Greenfield, and WT Robinson. "Halogenated Terpenoids. XXII. Uroterpenol. the C8 Stereochemistry." Australian Journal of Chemistry 39, no. 1 (1986): 21. http://dx.doi.org/10.1071/ch9860021.

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The two diastereoisomeric p-menth-1-ene-8,9-diols ( uroterpenols ) have been separated and crystallized. A crystallographic analysis of a dibromo derivative enables relative and absolute configurations to be assigned throughout the series.

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42

Aímola, Túlio J., Dimas J. P. Lima, Luiz C. Dias, Cláudio F. Tormena, and Marco A. B. Ferreira. "1H chemical shift differences of Prelog–Djerassi lactone derivatives: DFT and NMR conformational studies." Organic & Biomolecular Chemistry 13, no. 7 (2015): 2140–45. http://dx.doi.org/10.1039/c4ob02446j.

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This work reports an experimental and theoretical study of the conformational preferences of several Prelog–Djerassi lactone derivatives, to elucidate the<sup>1</sup>H NMR chemical shift differences in the lactonic core that are associated with the relative stereochemistry of these derivatives.

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43

Ola, Antonius R. B., Anna-Marie Babey, Cherie Motti, and Bruce F. Bowden. "Aplysiols C - E, Brominated Triterpene Polyethers from the Marine Alga Chondria armata and a Revision of the Structure of Aplysiol B." Australian Journal of Chemistry 63, no. 6 (2010): 907. http://dx.doi.org/10.1071/ch10081.

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Three new brominated triterpene polyethers, aplysiols C–E (1–3), were isolated from extracts of the red alga Chondria armata. Structures were determined by comparison with the closely related metabolite, aplysiol B, which was previously reported from the anaspidean mollusc Aplysia dactylomela. The relative stereochemistry of the tetracyclic ring system was determined from 1D gradient selective NOESY experiments and from biogenetic considerations that support a revision of the stereochemistry proposed for aplysiol B. In addition, three known brominated C15 acetogenin acetylenic ethers: (–)-pinn

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44

Afshari, M., M. Guiliano, G. Leandri, and H. Monti. "GC/FT-IR Determination of the Relative Configuration of Spiro [2.n] Methylenecyclopropyl Carbinols Diastereoisomeric Pairs." Applied Spectroscopy 46, no. 10 (1992): 1483–87. http://dx.doi.org/10.1366/000370292789619331.

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The reaction of l-methylene-2-trimethylsilyl spiro[2.n] alkanes with aldehydes under almost neutral conditions using tetrabutylammonium fluoride is consistent with 80% of diastereoisomeric pairs of spiromethylene cyclopropyl carbinols. This study elucidates the stereochemistry of these alcohols using the GC/FT-IR technique for inseparable mixtures and FT-IR dilution technique for a separable pair.

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45

Chesterton, Amy K. S., Sarah F. Jenkinson, Nigel A. Jones, George W. J. Fleet, and David J. Watkin. "(2S,4S)-4-Azido-1-benzyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrrolidine." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (2006): o2983—o2985. http://dx.doi.org/10.1107/s1600536806023105.

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The relative stereochemistry of the title compound, C16H22N4O2, a key intermediate in the synthesis of 3-deoxy imino sugars, was firmly established by X-ray crystallographic analysis. The absolute configuration was inferred from the starting material, D-galactose. There are no unusual crystal packing features.

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46

Montenegro-Sustaita, Mabel M., Hugo A. Jiménez-Vázquez, Elena Vargas-Díaz, J. Enrique Herbert-Pucheta, and L. Gerardo Zepeda-Vallejo. "Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products." Molecules 27, no. 9 (2022): 2810. http://dx.doi.org/10.3390/molecules27092810.

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A representative number of decalin and hydrindane derivatives 2a–l were prepared in 11–91% yield by means of a cascade reaction of cyclohexanone/cyclopentanone enolates and methyl acrylate through a Michael–Michael ring closure (MIMIRC) process. The relative stereochemistry of the four stereogenic centers formed in all products was determined by analyzing the vicinal coupling constants from the 1H NMR and X-ray crystallography. Such a stereochemical outcome was corroborated by conformational analysis supported by DFT calculations and simulating the 1H NMR spectra of representative products. Al

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Mackay, MF, M. Campbell та MJ Mcleish. "The Crystal Structure of Dimethyl (1aα,2aα,5β,6aβ-Hexahydroazirino[2,1-b]benzoxazole-1a, 5(1H)-dicarboxylate". Australian Journal of Chemistry 44, № 8 (1991): 1145. http://dx.doi.org/10.1071/ch9911145.

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The title compound formed the major component in a rearrangement of an analogue of 4-amino-4-deoxychorismic acid (1), an intermediate in the chorismate-p-aminobenzoic acid biotransformation. X-Ray crystallographic analysis has defined the relative stereochemistry at the four chiral centres in the tricyclic molecule.

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48

Tovar-Miranda, Ricardo, Raúl Cortés-García, Norma F. Santos-Sánchez, and Pedro Joseph-Nathan. "Isolation, Total Synthesis, and Relative Stereochemistry of a Dihydrofurocoumarin fromDorstenia contrajerva." Journal of Natural Products 61, no. 10 (1998): 1216–20. http://dx.doi.org/10.1021/np9801209.

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Arteaga, Jesús F., Victoriano Domingo, José F. Quílez del Moral, and Alejandro F. Barrero. "First Total Synthesis of (−)-Achilleol B: Reassignment of Its Relative Stereochemistry." Organic Letters 10, no. 9 (2008): 1723–26. http://dx.doi.org/10.1021/ol800326n.

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Poch, G. "Relative stereochemistry of fumonisin B1 at C-2 and C-3." Tetrahedron Letters 35, no. 41 (1994): 7707–10. http://dx.doi.org/10.1016/s0040-4039(00)77352-7.

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