Carotenoids and related polyenes. Part 7. Total synthesis of crassostreaxanthin B applying the stereoselective rearrangement of tetrasubstituted epoxides

Chisato Tode; Yumiko Yamano; Masayoshi Ito

doi:10.1039/B108037G

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Carotenoids and related polyenes. Part 7.¹ Total synthesis of crassostreaxanthin B applying the stereoselective rearrangement of tetrasubstituted epoxides†

Chisato Tode,^a Yumiko Yamano^a and Masayoshi Ito*^a

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* Corresponding authors

^a Kobe Pharmaceutical University, Motoyamakita-machi, Higashinada-ku, Kobe, 658-8558, Japan

Abstract

(3R,3′S)- and (3R,3′R)-Crassostreaxanthin B isomers are synthesized by application of the stereoselective rearrangement of tetrasubstituted epoxides 5a,b. As a result, the absolute configuration at C-3′ of 1 is determined to be S.

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Article information

DOI: https://doi.org/10.1039/B108037G
Article type: Paper
Submitted: 05 Sep 2001
Accepted: 29 Oct 2001
First published: 23 Nov 2001

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J. Chem. Soc., Perkin Trans. 1, 2001, 3338-3345

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Carotenoids and related polyenes. Part 7. Total synthesis of crassostreaxanthin B applying the stereoselective rearrangement of tetrasubstituted epoxides

C. Tode, Y. Yamano and M. Ito, J. Chem. Soc., Perkin Trans. 1, 2001, 3338 DOI: 10.1039/B108037G

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Journal of the Chemical Society, Perkin Transactions 1