Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides

Yumiko Yamano; Masayoshi Ito

doi:10.1039/B710386G

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Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides†‡

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
E-mail: y-yamano@kobepharma-u.ac.jp
Fax: +81 78 441 7562
Tel: +81 78 441 7562

Abstract

The synthesis of capsanthin 1 and capsorubin 2 was accomplished via the C₁₅-cyclopentyl ketone 6 prepared by Lewis acid-promoted regio- and stereoselective rearrangement of the epoxy dienal 5.

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Supplementary files

Synthesis and characterization data of compounds 7d–f, 8d, 8f, 9d, 9e, 11, 14–17 and 5, and spectral data of compounds 1 and 2 PDF (147K)

Article information

DOI: https://doi.org/10.1039/B710386G
Article type: Paper
Submitted: 09 Jul 2007
Accepted: 06 Aug 2007
First published: 29 Aug 2007

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Org. Biomol. Chem., 2007,5, 3207-3212

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Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides

Y. Yamano and M. Ito, Org. Biomol. Chem., 2007, 5, 3207 DOI: 10.1039/B710386G

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Organic & Biomolecular Chemistry

Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides†‡

Abstract

Supplementary files

Article information

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Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides

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