Total Synthesis of (−)-Enigmazole A

Keisuke Sakurai; Makoto Sasaki; Haruhiko Fuwa

doi:10.1002/anie.201801561

Total Synthesis of (−)-Enigmazole A

Keisuke Sakurai, Makoto Sasaki, Haruhiko Fuwa

生命科学研究科・分子化学生物学専攻

研究成果: Article › 査読

23 被引用数 (Scopus)

抄録

Total synthesis of (−)-enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross-metathesis/intramolecular oxa-Michael addition of a δ-hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold-catalyzed rearrangement of a propargylic benzoate, followed by ring-closing metathesis of the resultant α,β-unsaturated ketone.

本文言語	English
ページ（範囲）	5143-5146
ページ数	4
ジャーナル	Angewandte Chemie - International Edition
巻	57
号	18
DOI	https://doi.org/10.1002/anie.201801561
出版ステータス	Published - 2018 4月 23

ASJC Scopus subject areas

触媒
化学 (全般)

UN SDG

この成果は、次の持続可能な開発目標に貢献しています

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title = "Total Synthesis of (−)-Enigmazole A",

abstract = "Total synthesis of (−)-enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross-metathesis/intramolecular oxa-Michael addition of a δ-hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold-catalyzed rearrangement of a propargylic benzoate, followed by ring-closing metathesis of the resultant α,β-unsaturated ketone.",

keywords = "macrocycles, metathesis, natural products, rearrangement, total synthesis",

author = "Keisuke Sakurai and Makoto Sasaki and Haruhiko Fuwa",

note = "Funding Information: We thank Dr. Kentaro Takada (The University of Tokyo) for technical advice and Keita Sakamoto (Tohoku University) for HPLC purification of synthetic (−)-enigmazole A. This work was financially supported by the Asahi Glass Foundation.",

year = "2018",

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doi = "10.1002/anie.201801561",

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AU - Sakurai, Keisuke

AU - Sasaki, Makoto

AU - Fuwa, Haruhiko

N1 - Funding Information: We thank Dr. Kentaro Takada (The University of Tokyo) for technical advice and Keita Sakamoto (Tohoku University) for HPLC purification of synthetic (−)-enigmazole A. This work was financially supported by the Asahi Glass Foundation.

PY - 2018/4/23

Y1 - 2018/4/23

N2 - Total synthesis of (−)-enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross-metathesis/intramolecular oxa-Michael addition of a δ-hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold-catalyzed rearrangement of a propargylic benzoate, followed by ring-closing metathesis of the resultant α,β-unsaturated ketone.

AB - Total synthesis of (−)-enigmazole A, a marine macrolide natural product with cytotoxic activity, has been accomplished. The tetrahydropyran moiety was constructed by means of a domino olefin cross-metathesis/intramolecular oxa-Michael addition of a δ-hydroxy olefin. After coupling of advanced intermediates, the macrocycle was formed through gold-catalyzed rearrangement of a propargylic benzoate, followed by ring-closing metathesis of the resultant α,β-unsaturated ketone.

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KW - metathesis

KW - natural products

KW - rearrangement

KW - total synthesis

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JF - Angewandte Chemie - International Edition

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Total Synthesis of (−)-Enigmazole A

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ASJC Scopus subject areas

UN SDG

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