帕他霉素的合成研究：约翰逊中间体的合成。

Synthetic Studies on Pactamycin: A Synthesis of Johnson's Intermediate.

机构信息

School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

出版信息

Org Lett. 2020 May 1;22(9):3515-3518. doi: 10.1021/acs.orglett.0c00959. Epub 2020 Apr 22.

DOI:10.1021/acs.orglett.0c00959

PMID:32319784

Abstract

A formal total synthesis of pactamycin () has been accomplished by face-selective and regioselective nitroso Diels-Alder (NDA) reaction of acyl nitroso compound , which contains a camphorsultam chiral auxiliary, and chiral cyclopentadiene . Construction of the chiral secondary alcohol of was performed by (,)-Ts-DENEB catalyst-mediated reduction, and the NDA adduct was readily converted to Johnson's intermediate .

摘要

已通过包含樟脑磺内酰胺手性辅基的酰基亚硝基化合物与手性环戊二烯的面选择性和区域选择性亚硝-Diels-Alder（NDA）反应，完成了 pactamycin（）的全合成。通过（，）-Ts-DENEB 催化剂介导的还原，构建了的手性仲醇，NDA 加合物可轻易转化为 Johnson 的中间体。