Synthesis of both enantiomers of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas

Shigefumi Kuwahara; J. Ishikawa; W. S. Leal; S. Hamade; O. Kodama

doi:10.1055/s-2000-8228

Synthesis of both enantiomers of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas

Shigefumi Kuwahara, J. Ishikawa, W. S. Leal, S. Hamade, O. Kodama

AGR - Bioscience and Biotechnology for Future Bioindustries

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

19 Citations (Scopus)

Abstract

Synthesis of both enantiomers of a novel sesquiterpene, isolated as the putative sex pheromone of a Brazilian predatory stink bug (Tynacantha matginata Dallas) and proposed to have an unprecedented tricyclic carbon framework, was accomplished through an intramolecular Diels-Alder cyclization of a single optically active triene intermediate and separation of a pair of structural isomers derived from the resulting cycloadducts.

Original language	English
Pages (from-to)	1930-1935
Number of pages	6
Journal	Synthesis
Issue number	13
DOIs	https://doi.org/10.1055/s-2000-8228
Publication status	Published - 2000 Jan 1

Keywords

Cyclopentadienes
Diels-Alder reactions
Pheromones
Terpenoids
Total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1055/s-2000-8228

Cite this

@article{25256af5455f46a0ba2e4c7e92994439,

title = "Synthesis of both enantiomers of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas",

abstract = "Synthesis of both enantiomers of a novel sesquiterpene, isolated as the putative sex pheromone of a Brazilian predatory stink bug (Tynacantha matginata Dallas) and proposed to have an unprecedented tricyclic carbon framework, was accomplished through an intramolecular Diels-Alder cyclization of a single optically active triene intermediate and separation of a pair of structural isomers derived from the resulting cycloadducts.",

keywords = "Cyclopentadienes, Diels-Alder reactions, Pheromones, Terpenoids, Total synthesis",

author = "Shigefumi Kuwahara and J. Ishikawa and Leal, {W. S.} and S. Hamade and O. Kodama",

year = "2000",

month = jan,

day = "1",

doi = "10.1055/s-2000-8228",

language = "English",

pages = "1930--1935",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "13",

}

TY - JOUR

T1 - Synthesis of both enantiomers of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas

AU - Kuwahara, Shigefumi

AU - Ishikawa, J.

AU - Leal, W. S.

AU - Hamade, S.

AU - Kodama, O.

PY - 2000/1/1

Y1 - 2000/1/1

N2 - Synthesis of both enantiomers of a novel sesquiterpene, isolated as the putative sex pheromone of a Brazilian predatory stink bug (Tynacantha matginata Dallas) and proposed to have an unprecedented tricyclic carbon framework, was accomplished through an intramolecular Diels-Alder cyclization of a single optically active triene intermediate and separation of a pair of structural isomers derived from the resulting cycloadducts.

AB - Synthesis of both enantiomers of a novel sesquiterpene, isolated as the putative sex pheromone of a Brazilian predatory stink bug (Tynacantha matginata Dallas) and proposed to have an unprecedented tricyclic carbon framework, was accomplished through an intramolecular Diels-Alder cyclization of a single optically active triene intermediate and separation of a pair of structural isomers derived from the resulting cycloadducts.

KW - Cyclopentadienes

KW - Diels-Alder reactions

KW - Pheromones

KW - Terpenoids

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=0033693989&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033693989&partnerID=8YFLogxK

U2 - 10.1055/s-2000-8228

DO - 10.1055/s-2000-8228

M3 - Article

AN - SCOPUS:0033693989

SP - 1930

EP - 1935

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 13

ER -

Synthesis of both enantiomers of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this