Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar

Takashi Nakahata; Yohsuke Satoh; Shigefumi Kuwahara

doi:10.1016/j.tetlet.2008.02.039

Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar

Takashi Nakahata, Yohsuke Satoh, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The first enantioselective synthesis of (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a potent antifeedant isolated from the Japanese cedar, Cryptomeria japonica, was achieved starting from methyl (R)-4-hydroxy-3-methylbutanoate via a stereoselective carbonyl ene cyclization reaction as the key step. Comparison of the spectral data and specific rotation of the synthetic material with those of the natural product led to unambiguous stereochemical assignment of the antifeedant as 1S, 3R, and 6R.

Original language	English
Pages (from-to)	2438-2441
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2008.02.039
Publication status	Published - 2008 Apr 7

Keywords

Antifeedant
Bisabolane
Carbonyl ene reaction
Enantioselective synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "The first enantioselective synthesis of (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a potent antifeedant isolated from the Japanese cedar, Cryptomeria japonica, was achieved starting from methyl (R)-4-hydroxy-3-methylbutanoate via a stereoselective carbonyl ene cyclization reaction as the key step. Comparison of the spectral data and specific rotation of the synthetic material with those of the natural product led to unambiguous stereochemical assignment of the antifeedant as 1S, 3R, and 6R.",

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AU - Nakahata, Takashi

AU - Satoh, Yohsuke

AU - Kuwahara, Shigefumi

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AB - The first enantioselective synthesis of (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a potent antifeedant isolated from the Japanese cedar, Cryptomeria japonica, was achieved starting from methyl (R)-4-hydroxy-3-methylbutanoate via a stereoselective carbonyl ene cyclization reaction as the key step. Comparison of the spectral data and specific rotation of the synthetic material with those of the natural product led to unambiguous stereochemical assignment of the antifeedant as 1S, 3R, and 6R.

KW - Antifeedant

KW - Bisabolane

KW - Carbonyl ene reaction

KW - Enantioselective synthesis

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