Synthetic Studies of Isoschizogamine: Alternative Preparation of the Key Intermediate

被引：2

作者：

Hayashi, Noriyuki ^{[1
]}

Miura, Yusuke ^{[1
]}

Yokoshima, Satoshi ^{[2
]}

Fukuyama, Tohru ^{[2
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan

[2] Nagoya Univ, Grad Sch Pharmaceut Sci, Chikusa Ku, Furo Cho, Nagoya, Aichi 4648601, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2019年 / 67卷 / 01期

基金：

日本学术振兴会;

关键词：

alkaloid; lactone; quaternary carbon; rearrangement; total synthesis; AUS SCHIZOZYGIA CAFFAEOIDES; CORE; 1,4-ADDITION; CONSTRUCTION; ALDEHYDES;

D O I：

10.1248/cpb.c18-00718

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An alternative synthetic route toward a key intermediate in the total synthesis of isoschizogamine is described. The Claisen-Johnson rearrangement stereoselectively constructed a quaternary carbon. Trifluo-roperacetic acid mediated the Baeyer-Villiger oxidation to form a bicyclic lactone. The Mukaiyama-Matsuo protocol converted the lactone into an alpha,beta-unsaturated lactone, that was used as the substrate for the rhodium-mediated 1,4-addition of an arylboronic acid.

引用

页码：64 / 70

页数：7

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