Carotenoids and related polyenes. Part 8. Total synthesis of optically active mytiloxanthin applying the stereoselective rearrangement of tetrasubstituted epoxide

Chisato Tode; Yumiko Yamano; Masayoshi Ito

doi:10.1039/B201228F

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Carotenoids and related polyenes. Part 8.¹ Total synthesis of optically active mytiloxanthin applying the stereoselective rearrangement of tetrasubstituted epoxide†

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

Biomimetic synthesis of mytiloxanthin 1 was accomplished with stereoselective rearrangement of the tetrasubstituted epoxide 5 as a key reaction. This is the first total synthesis of optically active all-E mytiloxanthin 1.

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Article information

DOI: https://doi.org/10.1039/B201228F
Article type: Paper
Submitted: 01 Feb 2002
Accepted: 14 May 2002
First published: 06 Jun 2002

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J. Chem. Soc., Perkin Trans. 1, 2002, 1581-1587

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Carotenoids and related polyenes. Part 8. Total synthesis of optically active mytiloxanthin applying the stereoselective rearrangement of tetrasubstituted epoxide

C. Tode, Y. Yamano and M. Ito, J. Chem. Soc., Perkin Trans. 1, 2002, 1581 DOI: 10.1039/B201228F

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Journal of the Chemical Society, Perkin Transactions 1