对映-呋喃香豆素C的不对称合成。

Asymmetric synthesis of ent-fragransin C.

作者信息

Chaimanee Santikorn, Pohmakotr Manat, Kuhakarn Chutima, Reutrakul Vichai, Soorukram Darunee

机构信息

Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.

出版信息

Org Biomol Chem. 2017 May 10;15(18):3985-3994. doi: 10.1039/c7ob00749c.

DOI:10.1039/c7ob00749c

PMID:28443880

Abstract

The first asymmetric synthesis of ent-fragransin C was reported. The key step involves an intramolecular C-O bond formation (furan ring formation) via chemoselective generation of the benzylic carbocation leading to the 2,3-anti-3,4-syn-4,5-anti-tetrahydrofuran moiety as a single diastereomer in good yield. Our synthesis confirms that ent-fragransin C possesses 2R,3R,4S,5S configurations.

摘要

首次报道了对映-香豆素C的不对称合成。关键步骤涉及通过苄基碳正离子的化学选择性生成进行分子内C-O键形成（呋喃环形成），以良好的产率得到单一非对映异构体的2,3-反式-3,4-顺式-4,5-反式四氢呋喃部分。我们的合成证实对映-香豆素C具有2R,3R,4S,5S构型。