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Title: Total Synthesis of (-)-Sigillin A: A Polychlorinated and Polyoxygenated Natural Product
Authors: Yamaoka, Yousuke
Nakayama, Takamori
Kawai, Shota
Takasu, Kiyosei
Author's alias: 山岡, 庸介
高須, 清誠
Issue Date: 2-Oct-2020
Publisher: American Chemical Society
Journal title: Organic Letters
Volume: 22
Issue: 19
Start page: 7721
End page: 7724
Abstract: The total synthesis of (−)-sigillin A, a highly chlorinated and oxygenated octahydroisocoumarin, is described herein. A hexahydroisocoumarin skeleton was constructed from (R)-4-(trichloromethyl)oxetan-2-one in seven steps. Its unique manganese oxidation provided an enone as the key intermediate of sigillin A. Stereoselective installation of two hydroxy groups and formation of gem-dichloroalkene from the corresponding ketone led to the total synthesis of (−)-sigillin A in a total of 16 steps.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
The full-text file will be made open to the public on 16 September 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI(Published Version): 10.1021/acs.orglett.0c02930
PubMed ID: 32935991
Appears in Collections:Journal Articles

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