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

^*この研究の対応する著者

研究成果: Article › 査読

25 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	3175-3177
ページ数	3
ジャーナル	Angewandte Chemie - International Edition
巻	43
号	24
DOI	https://doi.org/10.1002/anie.200454212
出版ステータス	Published - 2004 6月 14
外部発表	はい

ASJC Scopus subject areas

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化学 (全般)

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10.1002/anie.200454212

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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.",

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author = "Yoshihisa Murata and Tomoyuki Kamino and Toshiaki Aoki and Seijiro Hosokawa and Susumu Kobayashi",

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AU - Kamino, Tomoyuki

AU - Aoki, Toshiaki

AU - Hosokawa, Seijiro

AU - Kobayashi, Susumu

PY - 2004/6/14

Y1 - 2004/6/14

N2 - 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.

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.

KW - Alcohols

KW - Aldol reaction

KW - Lactones

KW - Natural products

KW - Total synthesis

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JF - Angewandte Chemie - International Edition

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Highly efficient total synthesis of (+)-citreoviral

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