Academic literature on the topic 'Spiroketal synthesis'

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Journal articles on the topic "Spiroketal synthesis"

1

Tlais, Sami F., and Gregory B. Dudley. "On the proposed structures and stereocontrolled synthesis of the cephalosporolides." Beilstein Journal of Organic Chemistry 8 (August 14, 2012): 1287–92. http://dx.doi.org/10.3762/bjoc.8.146.

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The synthesis of four candidate stereoisomers of cephalosporolide H is described, made possible by a zinc-chelation strategy for controlling the stereochemistry of oxygenated 5,5-spiroketals. The same strategy likewise enables the first stereocontrolled synthesis of cephalosporolide E, which is typically isolated and prepared admixed with its spiroketal epimer, cephalosporolide F.
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2

Brimble, Margaret A., and Seng H. Chan. "Synthesis of 7-Methoxy-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-pyran]-3-one and 5,7-Dimethoxy-3′,4′,5′,6′-tetrahydrospiro[isobenzofuran-1(3H),2′-pyran]-3-one." Australian Journal of Chemistry 51, no. 3 (1998): 235. http://dx.doi.org/10.1071/c97193.

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The synthesis of novel aryl spiroketals, which contain a similar substitution pattern to that present in the antifungal agents the papulacandins, is described. Thus, spiroketal (7) was obtained from acid-catalysed cyclization of the keto alcohol (13), and spiroketal (8) was obtained from acid-catalysed cyclization of keto alcohols (12) and (19). Keto alcohols (12), (13) and (19) in turn were prepared by ortho-directed lithiation of amides (10), (11) and oxazoline (17) respectively, followed by reaction with δ-valerolactone. Substitution of the aromatic ring occurred at the sterically hindered
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3

Messerle, Barbara A., and Khuong Q. Vuong. "Synthesis of spiroketals by iridium-catalyzed double hydroalkoxylation." Pure and Applied Chemistry 78, no. 2 (2006): 385–90. http://dx.doi.org/10.1351/pac200678020385.

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A highly efficient approach to the synthesis of spiroketals involves the double cyclization of alkynyl diols using transition-metal catalysts. The iridium complex [Ir(PyP)(CO)2]BPh4 where PyP = 1-[(2-diphenylphosphino)ethyl]pyrazole is an effective catalyst for promoting the formation of spiroketals via this double hydroalkoxylation reaction. The complex promotes the formation of a series of spiroketal products from alkynyl diol starting materials such as 3-ethynylpentane-1,5-diol and 2-(4-hydroxybut-1-ynyl)benzyl alcohol. Stereoselective cyclization occurs for 3-ethynylpentane-1,5-diol, 3-eth
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4

Tlais, Sami F., and Gregory B. Dudley. "A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals." Beilstein Journal of Organic Chemistry 7 (May 4, 2011): 570–77. http://dx.doi.org/10.3762/bjoc.7.66.

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A highly efficient synthesis of oxygenated 5,5-spiroketals was performed towards the synthesis of the cephalosporolides. Gold(I) chloride in methanol induced the cycloisomerization of a protected alkyne triol with concomitant deprotection to give a strategically hydroxylated 5,5-spiroketal, despite the potential for regiochemical complications and elimination to furan. Other late transition metal Lewis acids were less effective. The use of methanol as solvent helped suppress the formation of the undesired furan by-product. This study provides yet another example of the advantages of gold catal
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5

Čikoš, Ana, Irena Ćaleta, Dinko Žiher, et al. "Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A." Beilstein Journal of Organic Chemistry 11 (August 19, 2015): 1447–57. http://dx.doi.org/10.3762/bjoc.11.157.

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Three novel spiroketals were prepared by a one-pot transformation of 6-O-methyl-9(E)-hydroxyiminoerythronolide A. We present the formation of a [4.5]spiroketal moiety within the macrolide lactone ring, but also the unexpected formation of a 10-C=11-C double bond and spontaneous change of stereochemistry at position 8-C. As a result, a thermodynamically stable structure was obtained. The structures of two new diastereomeric, unsaturated spiroketals, their configurations and conformations, were determined by means of NMR spectroscopy and molecular modelling. The reaction kinetics and mechanistic
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6

McLeod, Michael C., Margaret A. Brimble, Dominea C. K. Rathwell, Zoe E. Wilson, and Tsz-Ying Yuen. "Synthetic approaches to [5,6]-benzannulated spiroketal natural products." Pure and Applied Chemistry 84, no. 6 (2011): 1379–90. http://dx.doi.org/10.1351/pac-con-11-08-06.

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Studies toward the synthesis of three biologically active [5,6]-benzannulated spiroketal natural products are described. The first total synthesis of paecilospirone is reported, employing a late-stage, pH-neutral spiroketalization. A formal synthesis of γ-rubromycin is described, where the spiroketal moiety is formed by delicate manipulation of the electronic properties of the spirocyclization precursor. Finally, model work toward the total synthesis of berkelic acid is summarized, introducing a novel Horner–Wadsworth–Emmons/oxa-Michael (HWE/oxa-M) cascade to access the spiroketal precursor.
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7

Quayle, Peter, Jeremy C. Conway, Andrew C. Regan, and Christopher J. Urch. "A Palladium Mediated Spiroketal Synthesis." HETEROCYCLES 67, no. 1 (2006): 85. http://dx.doi.org/10.3987/com-05-s(t)20.

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8

Elsley, David A., Donald MacLeod, John A. Miller, Peter Quayle, and Gareth M. Davies. "A palladium mediated spiroketal synthesis." Tetrahedron Letters 33, no. 3 (1992): 409–12. http://dx.doi.org/10.1016/s0040-4039(00)74144-x.

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9

Ramakrishna, Bandi, and Perali Ramu Sridhar. "Stereoselective synthesis of 1,6-dioxaspirolactones from spiro-cyclopropanecarboxylated sugars: total synthesis of dihydro-pyrenolide D." RSC Advances 5, no. 11 (2015): 8142–45. http://dx.doi.org/10.1039/c4ra16753h.

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A one-pot protocol for the stereoselective construction of γ-spiroketal γ-lactone frameworks from sugar derived spiro-cyclopropanecarboxylic acids involving a ring enlargement and cyclization reaction is revealed.
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10

Conway, Jeremy C., Peter Quayle, Andrew C. Regan, and Christopher J. Urch. "Palladium mediated spiroketal synthesis: application to pheromone synthesis." Tetrahedron 61, no. 50 (2005): 11910–23. http://dx.doi.org/10.1016/j.tet.2005.09.055.

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