A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)

Shigefumi Kuwahara; Daisuke Itoh; Walter Soares Leal; Osamu Kodama

doi:10.1016/S0040-4020(98)00696-6

A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)

Shigefumi Kuwahara, Daisuke Itoh, Walter Soares Leal, Osamu Kodama

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

6 Citations (Scopus)

Abstract

(2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.

Original language	English
Pages (from-to)	11421-11430
Number of pages	10
Journal	Tetrahedron
Volume	54
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4020(98)00696-6
Publication status	Published - 1998 Sep 17
Externally published	Yes

Keywords

Olefination
Pheromones
Sulfur compound
Terpenes and terpenoids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)",

abstract = "(2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.",

keywords = "Olefination, Pheromones, Sulfur compound, Terpenes and terpenoids",

author = "Shigefumi Kuwahara and Daisuke Itoh and Leal, {Walter Soares} and Osamu Kodama",

year = "1998",

month = sep,

day = "17",

doi = "10.1016/S0040-4020(98)00696-6",

language = "English",

volume = "54",

pages = "11421--11430",

journal = "Tetrahedron",

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number = "38",

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T1 - A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)

AU - Kuwahara, Shigefumi

AU - Itoh, Daisuke

AU - Leal, Walter Soares

AU - Kodama, Osamu

PY - 1998/9/17

Y1 - 1998/9/17

N2 - (2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.

AB - (2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.

KW - Olefination

KW - Pheromones

KW - Sulfur compound

KW - Terpenes and terpenoids

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DO - 10.1016/S0040-4020(98)00696-6

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)

Abstract

Keywords

ASJC Scopus subject areas

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