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

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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10.1016/j.tetlet.2008.02.039

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title = "Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar",

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.",

keywords = "Antifeedant, Bisabolane, Carbonyl ene reaction, Enantioselective synthesis",

author = "Takashi Nakahata and Yohsuke Satoh and Shigefumi Kuwahara",

note = "Funding Information: We are grateful to Professor Kim (Kochi University) for providing the copies of the NMR spectra of the natural antifeedant ( 1 ). We also thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 19380065).",

year = "2008",

month = apr,

day = "7",

doi = "10.1016/j.tetlet.2008.02.039",

language = "English",

volume = "49",

pages = "2438--2441",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar

AU - Nakahata, Takashi

AU - Satoh, Yohsuke

AU - Kuwahara, Shigefumi

N1 - Funding Information: We are grateful to Professor Kim (Kochi University) for providing the copies of the NMR spectra of the natural antifeedant ( 1 ). We also thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 19380065).

PY - 2008/4/7

Y1 - 2008/4/7

N2 - 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.

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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UR - http://www.scopus.com/inward/citedby.url?scp=40649090162&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.02.039

DO - 10.1016/j.tetlet.2008.02.039

M3 - Article

AN - SCOPUS:40649090162

VL - 49

SP - 2438

EP - 2441

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 15

ER -

Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar

Abstract

Keywords

ASJC Scopus subject areas

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