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Journal articles on the topic 'Sharpless dihydroxylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Devi, Runjun, and Sajal Kumar Das. "Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates." Beilstein Journal of Organic Chemistry 13 (March 21, 2017): 571–78. http://dx.doi.org/10.3762/bjoc.13.56.

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While the exploitation of the Sharpless asymmetric dihydroxylation as the source of chirality in the synthesis of acyclic molecules and saturated heterocycles has been tremendous, its synthetic utility toward chiral benzo-annulated heterocycles is relatively limited. Thus, in the search for wider applications of Sharpless asymmetric dihydroxylation-derived diols for the synthesis of benzo-annulated heterocycles, we report herein our studies in the asymmetric synthesis of (R)-1-((R)-6-fluorochroman-2-yl)ethane-1,2-diol, (R)-1-((S)-6-fluorochroman-2-yl)ethane-1,2-diol and (S)-6-fluoro-2-((R)-oxi

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2

Dethe, Dattatraya H., and Vijay Kumar B. "Concise asymmetric total synthesis of bruceolline J." Organic Chemistry Frontiers 2, no. 5 (2015): 548–51. http://dx.doi.org/10.1039/c5qo00030k.

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3

Lu, Kui, Ming Li, Yuna Huang, et al. "Total synthesis of wikstrol A and wikstrol B." Organic & Biomolecular Chemistry 17, no. 35 (2019): 8206–13. http://dx.doi.org/10.1039/c9ob01219b.

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4

Wöltinger, Jens, Hans Henniges, Hans-Peter Krimmer, Andreas S. Bommarius, and Karlheinz Drauz. "Application of the continuous Sharpless dihydroxylation." Tetrahedron: Asymmetry 12, no. 15 (2001): 2095–98. http://dx.doi.org/10.1016/s0957-4166(01)00355-x.

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5

Senapati, Sibadatta, and Chepuri V. Ramana. "A concise/catalytic approach for the construction of the C14–C28 fragment of eribulin." Organic & Biomolecular Chemistry 19, no. 20 (2021): 4542–50. http://dx.doi.org/10.1039/d1ob00661d.

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A diastereoselective gold cyclisation and a Sharpless asymmetric dihydroxylation–cycloetherification protocol were carried out for the construction of the key disaccharide unit (C14–C28) of eribulin mesylate with a linear sequence of 14 steps.

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6

Talero, Alexánder, та Antonio Burtoloso. "Sharpless Asymmetric Dihydroxylation on α,β-Unsaturated Diazoketones: A New Entry for the Synthesis of Disubstituted Furanones". Synlett 28, № 14 (2017): 1748–52. http://dx.doi.org/10.1055/s-0036-1590977.

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The synthesis of enantiomerically pure 4,5-disubstituted 2-furanones is accomplished in three steps from aldehydes. The steps involve a highly enantioselective Sharpless asymmetric dihydroxylation of α,β-unsaturated diazoketones, followed by a photochemical Wolff rearrangement.

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7

Philippo, Christophe M. G., Patrick Mougenot, Alain Braun, Gérard Defosse, Stéphanie Auboussier, and Philippe R. Bovy. "Enantioselective Sharpless Dihydroxylation of Vinylic Aromatic Heterocycles." Synthesis 2000, no. 01 (2000): 127–34. http://dx.doi.org/10.1055/s-2000-6237.

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8

Ahrgren, Leif, and Lori Sutin. "Sharpless Asymmetric Dihydroxylation on an Industrial Scale." Organic Process Research & Development 1, no. 6 (1997): 425–27. http://dx.doi.org/10.1021/op970030v.

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9

Iwashima, Makoto, Takeshi Kinsho, and Amos B. Smith. "A caveat on the Sharpless asymmetric dihydroxylation." Tetrahedron Letters 36, no. 13 (1995): 2199–202. http://dx.doi.org/10.1016/0040-4039(95)00274-g.

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10

Nookaraju, U., Eeshwaraiah Begari, and Pradeep Kumar. "Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation–lactonization approach." Org. Biomol. Chem. 12, no. 31 (2014): 5973–80. http://dx.doi.org/10.1039/c4ob00965g.

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A simple and novel synthesis of (+)-monocerin was achieved from 3-buten-1-ol employing HKR, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-S<sub>N</sub>2 cyclization and a novel copper mediated tandem cyanation–cyclization as the key steps.

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11

Takamura, Hiroyoshi, Takayuki Fujiwara, Isao Kadota, and Daisuke Uemura. "Stereoselective synthesis of the C79–C97 fragment of symbiodinolide." Beilstein Journal of Organic Chemistry 9 (September 25, 2013): 1931–35. http://dx.doi.org/10.3762/bjoc.9.228.

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Symbiodinolide is a polyol marine natural product with a molecular weight of 2860. Herein, a streamlined synthesis of the C79–C97 fragment of symbiodinolide is described. In the synthetic route, a spiroacetalization, a Julia–Kocienski olefination, and a Sharpless asymmetric dihydroxylation were utilized as the key transformations.

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12

Chandrasekhar, Srivari, Namdeo Gangathade, Kiranmai Nayani, Hemalatha Bukya, and Prathama S. Mainkar. "Scalable Synthesis of l-allo-Enduracididine: The Unusual Amino Acid Present in Teixobactin." Synlett 32, no. 14 (2021): 1465–68. http://dx.doi.org/10.1055/a-1528-0625.

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AbstractA scalable synthesis of l-allo-enduracididine is achieved from commercially available (S)-glycidol in ten linear steps involving well-established synthetic transformations. The synthetic route is flexible and can be used to synthesize all four diastereomers by changing the stereochemistry of glycidol and Sharpless asymmetric dihydroxylation reagent.

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13

Wang, JinXin, ChaoXin Zhang, Ying Li, and QiDong You. "An efficient synthesis of an optically active (-)-(3R, 4R, 5R)-4-(1-hydroxyl-isopropyl)-3-acetyloxyl-butyrolactone." Journal of Chemical Research 2005, no. 10 (2005): 665–68. http://dx.doi.org/10.3184/030823405774663093.

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An optically active β-hydroxyl–γ-butyrolactone was synthesised from nonchiral starting material by employing reductive cleavage reaction, Sharpless asymmetric epoxidation and dihydroxylation as key steps. This strategy can be used to prepare many chiral β-hydroxyl–γ-butyrolactone analogues. The crystal structure of 10 was determined by X-ray crystallographs.

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14

Mehltretter, Gerald M., Christian Döbler, Uta Sundermeier, and Matthias Beller. "An improved version of the Sharpless asymmetric dihydroxylation." Tetrahedron Letters 41, no. 42 (2000): 8083–87. http://dx.doi.org/10.1016/s0040-4039(00)01396-4.

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15

Eames, Jason, Helen J. Mitchell, Adam Nelson, Peter O’Brien, Stuart Warren, and Paul Wyatt. "An efficient protocol for Sharpless-style racemic dihydroxylation." Journal of the Chemical Society, Perkin Transactions 1, no. 8 (1999): 1095–104. http://dx.doi.org/10.1039/a900277d.

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16

Woeltinger, Jens, Hans Henniges, Hans-Peter Krimmer, Andreas S. Bommarius, and Karlheinz Drauz. "ChemInform Abstract: Application of the Continuous Sharpless Dihydroxylation." ChemInform 33, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.200206043.

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17

Paterson, Ian, Edward A. Anderson, Stephen M. Dalby, et al. "Progress toward a total synthesis of spirastrellolide A." Pure and Applied Chemistry 79, no. 4 (2007): 667–76. http://dx.doi.org/10.1351/pac200779040667.

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Progress toward a total synthesis of spirastrellolide A, a 38-membered marine macrolide, is reported. Syntheses of two diastereomers of the C1-C25 region, and an evolving Sharpless dihydroxylation strategy toward a C26-C40 fragment, are described. The syntheses exploit boron-mediated aldol chemistry to install key stereocenters, and feature late-stage thermodynamically controlled spiroacetalizations.

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18

Jew, Sang-sup, Hyun-ah Kim, Jeong-hoon Kim, and Hyeung-geun Park. "Enantioselective Synthesis of Eucomols Using Sharpless Catalytic Asymmetric Dihydroxylation." HETEROCYCLES 46, no. 1 (1997): 65. http://dx.doi.org/10.3987/com-97-s24.

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19

Philippo, Christophe M. G., Patrick Mougenot, Alain Braun, Gerard Defosse, Stephanie Auboussier, and Philippe R. Bovy. "ChemInform Abstract: Enantioselective Sharpless Dihydroxylation of Vinylic Aromatic Heterocycles." ChemInform 31, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.200015029.

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20

Salvadori, Piero, Stefano Superchi, and Filippo Minutolo. "Anomalous Face-Selectivity in Sharpless Asymmetric Dihydroxylation ofo-Allylbenzamides." Journal of Organic Chemistry 61, no. 13 (1996): 4190–91. http://dx.doi.org/10.1021/jo9607323.

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21

Christie, Hamish S., David P. G. Hamon, and Kellie L. Tuck. "Concerning kinetic resolution by the Sharpless asymmetric dihydroxylation reaction." Chemical Communications, no. 19 (1999): 1989–90. http://dx.doi.org/10.1039/a906423k.

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22

Eames, Jason, Helen J. Mitchell, Adam Nelson, Peter O'Brien, Stuart Warren, and Paul Wyatt. "An efficient protocol for a sharpless style racemic dihydroxylation." Tetrahedron Letters 36, no. 10 (1995): 1719–22. http://dx.doi.org/10.1016/0040-4039(95)00054-g.

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23

Fairweather, Jon K., Robert V. Stick та D. Matthew G. Tilbrook. "The Asymmetric Dihydroxylation of Some Alkenyl 2-Acetylamino-2-deoxy-β-D-glucopyranosides: the Preparation of Optically Pure Epoxides as Putative Inhibitors of Chitinases". Australian Journal of Chemistry 51, № 6 (1998): 471. http://dx.doi.org/10.1071/c97175.

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Various alkenyl 2-acetylamino-2-deoxy-β-D-glucopyranosides have been subjected to the Sharpless asymmetric dihydroxylation protocol to yield the corresponding diols, albeit with somewhat disappointing stereoselectivity. An alternative, more traditional approach has yielded the optically pure epoxyalkyl 2-acetylamino-2-deoxy-β-D-glucopyranosides as putative inhibitors of chitinases. As well, an epoxypropyl chito-bioside and -trioside have been prepared, each as mixtures of two diastereoisomers.

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24

Ramana, Chepuri V., Sibadatta Senapati, Nivedya A. Unmesh, Manoj N. Shet, Iram Ahmad, and Nandu Ajikumar. "Unified Approach for the Total Synthesis of Bis-THF C15 Acetogenins: A Chloroenyne from Laurencia majuscula, Laurendecumenyne B and Laurefurenynes A/B." Synthesis 53, no. 16 (2021): 2903–10. http://dx.doi.org/10.1055/a-1500-1407.

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AbstractA highly diastereoselective total synthesis of several bis-THF C15 acetogenin natural products, chloroenyne from Laurencia majuscula, laurendecumenyne B, and laurefurenynes A/B, is reported. Additionally the synthesis of an advanced intermediate reported in the earlier total synthesis of (E/Z)-elatenynes (formal synthesis) is described. The salient features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, SN2 halogenation, and a relay cross metathesis.

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25

Ramana, L. V., M. Suri Appa Rao, K. M. Ch Apparao, and B. Nageswara Rao. "Enantio Selective Synthesis of New Phenylpropanoid: Isolated from Walsura trifoliata." Asian Journal of Chemistry 31, no. 9 (2019): 2042–46. http://dx.doi.org/10.14233/ajchem.2019.22064.

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A new phenylpropanoid containing flavon-3-ol has been isolated from the leaves of traditional medicinal plant, Walsura trifoliata. The structure of the compound was established on the basis of spectroscopic evidence [2D NMR, HREIMS] and by its alternative synthesis. The synthesis of this natural product was achieved from inexpensive and readily available starting materials of phloroglucinol dihydrate. Key reaction sequence includes Grubbs-II RCM reaction, Wittig reaction and sharpless dihydroxylation using AD-mix α.

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26

Ramanujan, Vyasabhattar, Shaik Sadikha, and Kumar Pavan. "Stereoselective synthesis of (-)-tetrahydropyrenophorol." Journal of the Serbian Chemical Society 85, no. 9 (2020): 1129–36. http://dx.doi.org/10.2298/jsc190823040r.

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Tetrahydropyrenophorol, an interesting macrodiolide, was isolated from the plant Fagonia cretica. The total synthesis of (?)-1-tetrahydropyrenophorol was achieved in an elegant and linear manner from readily an accessible racemic epoxide. The archetypal reactions include regioselective opening of the epoxide, Sharpless asymmetric dihydroxylation, and Mitsunobu cyclodimerization to construct the requisite 16-membered bis-lactone. The synthetic approach demonstrated here is very simple and could be used for the syntheses of related compounds in an economic and highly stereoselective way.

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27

Wierzejska, Jolanta, Shin-ichi Motogoe, Yuto Makino, Tetsuya Sengoku, Masaki Takahashi, and Hidemi Yoda. "A new approach toward the total synthesis of (+)-batzellaside B." Beilstein Journal of Organic Chemistry 8 (October 25, 2012): 1831–38. http://dx.doi.org/10.3762/bjoc.8.210.

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A new synthetic approach to (+)-batzellaside B from naturally abundant L-pyroglutamic acid is presented in this article. The key synthetic step involves Sharpless asymmetric dihydroxylation of an olefinic substrate functionalized with an acetoxy group to introduce two chiral centres diastereoselectively into the structure. Heterocyclic hemiaminal 4, which could be converted from the resulting product, was found to provide stereospecific access to enantiomerically enriched allylated intermediate, offering better prospects for the total synthesis of this natural product.

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28

Nichols, Christopher J., and Melissa R. Taylor. "The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory." Journal of Chemical Education 82, no. 1 (2005): 105. http://dx.doi.org/10.1021/ed082p105.

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29

Zhang, Yan, and George A. O'Doherty. "Remote steric effect on the regioselectivity of Sharpless asymmetric dihydroxylation." Tetrahedron 61, no. 26 (2005): 6337–51. http://dx.doi.org/10.1016/j.tet.2005.03.119.

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30

Ko, Soo Y. "Cis-epoxides via sharpless' asymmetric dihydroxylation reaction: Synthesis of (+)-disparlure." Tetrahedron Letters 35, no. 21 (1994): 3601–4. http://dx.doi.org/10.1016/s0040-4039(00)73251-5.

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31

Torii, Sigeru, Ping Liu, and Hideo Tanaka. "Electrochemical Os-Catalyzed Asymmetric Dihydroxylation of Olefins with Sharpless’ Ligand." Chemistry Letters 24, no. 4 (1995): 319–20. http://dx.doi.org/10.1246/cl.1995.319.

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32

Mehltretter, Gerald M., Christian Doebler, Uta Sundermeier, and Matthias Beller. "ChemInform Abstract: An Improved Version of the Sharpless Asymmetric Dihydroxylation." ChemInform 32, no. 2 (2001): no. http://dx.doi.org/10.1002/chin.200102034.

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33

Eames, Jason, Helen J. Mitchell, Adam Nelson, Peter O'Brien, Stuart Warren, and Paul Wyatt. "ChemInform Abstract: An Efficient Protocol for Sharpless-Style Racemic Dihydroxylation." ChemInform 30, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199934086.

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34

Sun, Jun, Song Fan, Zhan Wang, Guoning Zhang, Kai Bao, and Weige Zhang. "The total synthesis of D-chalcose and its C-3 epimer." Beilstein Journal of Organic Chemistry 9 (November 22, 2013): 2620–24. http://dx.doi.org/10.3762/bjoc.9.296.

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We completed a new and efficient synthesis of D-chalcose (I) and the first synthesis of its C-3 epimer (I′) in nine steps with overall yields of 23% and 24%, respectively. The key steps in the sequence were the formation of the stereocenter on C3 via Grignard reaction, the introduction of the stereogenic center on C2 by Sharpless asymmetric dihydroxylation, the protection of the C1 and C2 hydroxy groups with tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf), and the selective cleavage of the primary OTBS ether using catalytic DL-10-camphorsulfonic acid (CSA) in MeOH.

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35

Borah, Arun Jyoti, Progyashree Goswami, Nabin C. Barua, and Prodeep Phukan. "Synthesis of unit-B of cryptophycin-24 via Sharpless asymmetric dihydroxylation." Tetrahedron Letters 53, no. 52 (2012): 7128–30. http://dx.doi.org/10.1016/j.tetlet.2012.10.078.

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36

Ramón, Rosario, Mònica Alonso, and Antoni Riera. "A unified approach to mesityl amino acids based on Sharpless dihydroxylation." Tetrahedron: Asymmetry 18, no. 23 (2007): 2797–802. http://dx.doi.org/10.1016/j.tetasy.2007.10.041.

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37

Spivey, Alan C., R. Hanson, N. Scorah, and S. J. Thorpe. "Sharpless Asymmetric Dihydroxylation: Effect of Alkene Structure on Rates and Selectivity." Journal of Chemical Education 76, no. 5 (1999): 655. http://dx.doi.org/10.1021/ed076p655.

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38

Lapitskaya, Margarita A., Ljudmila L. Vasiljeva, Peter M. Demin, and Kasimir K. Pivnitsky. "Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation." Mendeleev Communications 14, no. 6 (2004): 287–90. http://dx.doi.org/10.1070/mc2004v014n06abeh002003.

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39

Blundell, Paul, Ashit K. Ganguly, and Viyyoor M. Girijavallabhan. "Synthesis of Novel Azole Antifungals by a Modified Sharpless Asymmetric Dihydroxylation." Synlett 1994, no. 04 (1994): 263–65. http://dx.doi.org/10.1055/s-1994-22820.

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40

JEW, S., H. KIM, J. KIM, and H. PARK. "ChemInform Abstract: Enantioselective Synthesis of Eucomols Using Sharpless Catalytic Asymmetric Dihydroxylation." ChemInform 29, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199818254.

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41

EAMES, J., H. J. MITCHELL, A. NELSON, P. O'BRIEN, S. WARREN, and P. WYATT. "ChemInform Abstract: An Efficient Protocol for a Sharpless Style Racemic Dihydroxylation." ChemInform 26, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199538094.

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42

Han, Hyunsoo, and Kim D. Janda. "Multipolymer-Supported Substrate and Ligand Approach to the Sharpless Asymmetric Dihydroxylation." Angewandte Chemie International Edition in English 36, no. 16 (1997): 1731–33. http://dx.doi.org/10.1002/anie.199717311.

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43

Chen, Fen-Er, Qiu-Qin He, Zhong-Hua Wang, Chen Zheng, Feng Li, and Lei Zhao. "An Efficient Enantioselective Synthesis of Florfenicol Based on Sharpless Asymmetric Dihydroxylation." Synthesis 44, no. 05 (2012): 699–704. http://dx.doi.org/10.1055/s-0031-1289706.

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44

Jew, Sang-sup, Kwang-dae Ok, Hee-jin Kim, et al. "Enantioselective synthesis of 20(S)-camptothecin using sharpless catalytic asymmetric dihydroxylation." Tetrahedron: Asymmetry 6, no. 6 (1995): 1245–48. http://dx.doi.org/10.1016/0957-4166(95)00154-h.

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45

Sobti, Aditya, and Gary A. Sulikowski. "Synthesis of via a tandem sharpless asymmetric dihydroxylation/lipase-catalyzed transesterification." Tetrahedron Letters 36, no. 24 (1995): 4193–96. http://dx.doi.org/10.1016/0040-4039(95)00778-b.

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46

Laurenson, James A. B., John A. Parkinson, Jonathan M. Percy, Giuseppe Rinaudo, and Ricard Roig. "Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate." Beilstein Journal of Organic Chemistry 9 (November 26, 2013): 2660–68. http://dx.doi.org/10.3762/bjoc.9.301.

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Esters of crotonic acid were brominated on a multigramme scale using a free radical procedure. A phase transfer catalysed fluorination transformed these species to the 4-fluorobut-2E-enoates reproducibly and at scale (48–53%, ca. 300 mmol). Asymmetric dihydroxylation reactions were then used to transform the butenoate, ultimately into all four diastereoisomers of a versatile fluorinated C4 building block at high enantiomeric-enrichment. The (DHQ)2AQN and (DHQD)2AQN ligands described by Sharpless were the most effective. The development and optimisation of a new and facile method for the determ

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47

Heravi, Majid M., Vahideh Zadsirjan, Maryam Esfandyari, and Tahmineh Baie Lashaki. "Applications of sharpless asymmetric dihydroxylation in the total synthesis of natural products." Tetrahedron: Asymmetry 28, no. 8 (2017): 987–1043. http://dx.doi.org/10.1016/j.tetasy.2017.07.004.

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48

Dominique, Romyr, and René Roy. "Stereoselective synthesis of glycoclusters using an olefin metathesis and Sharpless dihydroxylation sequence." Tetrahedron Letters 43, no. 3 (2002): 395–98. http://dx.doi.org/10.1016/s0040-4039(01)02186-4.

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49

Nair, Sajiv K., Jean J. Matthews, Stephan J. Cripps, et al. "Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation." Tetrahedron Letters 51, no. 11 (2010): 1451–54. http://dx.doi.org/10.1016/j.tetlet.2009.12.092.

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50

Bonini, Carlo, Lucia Chiummiento, Margherita De Bonis, Maria Funicello, Paolo Lupattelli, and Rocco Pandolfo. "Application of Sharpless asymmetric dihydroxylation to thienyl- and benzothienyl acrylates and crotonates." Tetrahedron: Asymmetry 17, no. 20 (2006): 2919–24. http://dx.doi.org/10.1016/j.tetasy.2006.10.035.

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