Highly efficient total synthesis of (+)-citreoviral

Yoshihisa Murata; Tomoyuki Kamino; Toshiaki Aoki; Seijiro Hosokawa; Susumu Kobayashi

doi:10.1002/anie.200454212

Highly efficient total synthesis of (+)-citreoviral

Yoshihisa Murata, Tomoyuki Kamino, Toshiaki Aoki, Seijiro Hosokawa, Susumu Kobayashi

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

24 Citations (Scopus)

Abstract

Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S _N2 reaction of a tertiary alcohol to form intermediate 2.

Original language	English
Pages (from-to)	3175-3177
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	24
DOIs	https://doi.org/10.1002/anie.200454212
Publication status	Published - 2004 Jun 14
Externally published	Yes

Keywords

Alcohols
Aldol reaction
Lactones
Natural products
Total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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AU - Murata, Yoshihisa

AU - Kamino, Tomoyuki

AU - Aoki, Toshiaki

AU - Hosokawa, Seijiro

AU - Kobayashi, Susumu

PY - 2004/6/14

Y1 - 2004/6/14

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AB - Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimide, and an intramolecular S N2 reaction of a tertiary alcohol to form intermediate 2.

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KW - Aldol reaction

KW - Lactones

KW - Natural products

KW - Total synthesis

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