Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2001(11): 1737-1741
DOI: 10.1055/s-2001-16748
DOI: 10.1055/s-2001-16748
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
A Formal Catalytic Asymmetric Synthesis of (+)-Biotin with Modified Cinchona Alkaloids
Further Information
Received
14 June 2001
Publication Date:
28 September 2004 (online)
Publication History
Publication Date:
28 September 2004 (online)
Abstract
A formal catalytic asymmetric synthesis of (+)-biotin was realized. The key steps involve a catalytic, highly enantioselective and quantitative desymmetrization of a meso cyclic anhydride followed by a one-pot chemoselective reduction to form the optically active lactone intermediate in the Goldberg-Sternbach (+)-biotin synthesis.
Key words
biotin - vitamin - cinchona alkaloids - asymmetric catalysis - enantioselective desymmetrization
- 1
De Clercq PJ. Chem. Rev. 1997, 97: 1755 -
2a
Goldberg MW, andSternbach LH. inventors; US Patent 2489232. -
-
3a
Goldberg MW, andSternbach LH. inventors; US Patent 2489235. -
-
4a
Goldberg MW, andSternbach LH. inventors; US Patent 2489238. -
- 5
Field GF. J. Org. Chem. 1978, 43: 1084 -
6a
Isaka I.Kubo K.Takashima M.Murakami M. Yakugaku Zasshi 1968, 88: 964 -
7a
Holick W,Pauling H, andCottong NA. inventors; Eur. Patent. Appl. EP 0154225 A2. -
-
8a
Sumitomo Chemical Co. Ltd. Jpn. Kokai, Tokyo Koho JP 60100583, 1985.
-
- 9
Shimizu T.Seki M. Tetrahedron Lett. 2000, 41: 5099 - 10
Gerecke M.Zimmermann J.-P.Aschwanden W. Helv. Chim. Acta 1970, 53: 991 - 11
Matsuki K.Inoue H.Takeda M. Tetrahedron Lett. 1993, 34: 1167 - 12
Chen F.-E.Huang Y.-D.Fu H.Cheng Y.Zhang D.-M.Li Y.-Y.Peng Z.-Z. Synthesis 2000, 2004 - 13
Iriuchijima S.Hasegawa K.Tsuchihashi G. Agric. Biol. Chem. 1982, 46: 1907 - 14
Wang Y.-F.Sih CJ. Tetrahedron Lett. 1984, 25: 4999 - 15
Jaeschke G.Seebach D. J. Org. Chem. 1998, 63: 1190 - 16
Chen Y.Tian S.-K.Deng L. J. Am. Chem. Soc. 2000, 122: 9542 - 17
Theisen PD.Heathcock CH. J. Org. Chem. 1993, 58: 142 - 18
Yoon NM.Pak CS.Brown HC.Krishnamurthy S.Stocky TP. J. Org. Chem. 1973, 38: 2786 - 19
Falorni M.Porcheddu A.Taddei M. Tetrahedron Lett. 1999, 40: 4395 - 20
Lavielle S.Bory S.Moreau B.Luche MJ.Marquet A. J. Am. Chem. Soc. 1978, 100: 1558 - 21
Matsuki K.Inoue H.Ishida A.Takeda M.Nakagawa M.Hino T. Chem. Pharm. Bull. 1994, 42: 9 - 22
Shimizu M.Matsukawa K.Fujisawa T. Bull. Chem. Soc. Jpn. 1993, 66: 2128 - 23
Hiratake J.Inagaki M.Yamamoto Y.Oda J. J. Chem. Soc., Perkin. Trans. 1 1987, 1053