Synthesis of pteroenone and its stereoisomers, a defensive metabolite of the abducted antarctic pteropod clione antarctica

Hiroki Asao; Yoko Nakamura; Yukito Furuya; Shigefumi Kuwahara; Bill J. Baker; Hiromasa Kiyota

doi:10.1002/hlca.201000258

Synthesis of pteroenone and its stereoisomers, a defensive metabolite of the abducted antarctic pteropod clione antarctica

Hiroki Asao, Yoko Nakamura, Yukito Furuya, Shigefumi Kuwahara, Bill J. Baker, Hiromasa Kiyota

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

3 Citations (Scopus)

Abstract

Four stereoisomers of (+)-pteroenone, a defensive metabolite of the abducted Antarctic pteropod Clione antarctica, were synthesized by employing anti-/syn-selective aldol reactions as the key step. These compounds displayed no antifeedant activity against a generally benthic Antarctic fish that does not co-occur with this pteropod.

Original language	English
Pages (from-to)	1933-1944
Number of pages	12
Journal	Helvetica Chimica Acta
Volume	93
Issue number	10
DOIs	https://doi.org/10.1002/hlca.201000258
Publication status	Published - 2010 Oct

Keywords

Aldol reaction
Clione antarctica
Marine natural products
Metabolites
Pteroenone

ASJC Scopus subject areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1002/hlca.201000258

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abstract = "Four stereoisomers of (+)-pteroenone, a defensive metabolite of the abducted Antarctic pteropod Clione antarctica, were synthesized by employing anti-/syn-selective aldol reactions as the key step. These compounds displayed no antifeedant activity against a generally benthic Antarctic fish that does not co-occur with this pteropod.",

keywords = "Aldol reaction, Clione antarctica, Marine natural products, Metabolites, Pteroenone",

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T1 - Synthesis of pteroenone and its stereoisomers, a defensive metabolite of the abducted antarctic pteropod clione antarctica

AU - Asao, Hiroki

AU - Nakamura, Yoko

AU - Furuya, Yukito

AU - Kuwahara, Shigefumi

AU - Baker, Bill J.

AU - Kiyota, Hiromasa

PY - 2010/10

Y1 - 2010/10

N2 - Four stereoisomers of (+)-pteroenone, a defensive metabolite of the abducted Antarctic pteropod Clione antarctica, were synthesized by employing anti-/syn-selective aldol reactions as the key step. These compounds displayed no antifeedant activity against a generally benthic Antarctic fish that does not co-occur with this pteropod.

AB - Four stereoisomers of (+)-pteroenone, a defensive metabolite of the abducted Antarctic pteropod Clione antarctica, were synthesized by employing anti-/syn-selective aldol reactions as the key step. These compounds displayed no antifeedant activity against a generally benthic Antarctic fish that does not co-occur with this pteropod.

KW - Aldol reaction

KW - Clione antarctica

KW - Marine natural products

KW - Metabolites

KW - Pteroenone

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EP - 1944

JO - Helvetica Chimica Acta

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IS - 10

ER -

Synthesis of pteroenone and its stereoisomers, a defensive metabolite of the abducted antarctic pteropod clione antarctica

Abstract

Keywords

ASJC Scopus subject areas

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