穆阿霉素 C-C 片段的合成。

Synthesis of the C -C Fragment of Muamvatin.

机构信息

Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai, 400076, India.

出版信息

Chem Asian J. 2020 Jul 16;15(14):2208-2211. doi: 10.1002/asia.202000459. Epub 2020 Jun 12.

DOI:10.1002/asia.202000459

Abstract

This report delineates our efforts towards the synthesis of a stereochemically well-defined ketone, the C -C fragment of muamvatin, the first example of a 2, 4, 6-trioxaadamantane ring skeletal polypropionate marine natural product, using two non-aldol variants. i) The Shimizu reaction, a Pd(0) mediated stereoselective epoxy-ring opening of alkenyl oxiranes, was employed for the stereoselective installation of methyl groups in syn-fashion and ii) Bode's protocol, a NHC-mediated reaction on β-epoxy aldehydes, was utilized for stereoselective construction of methyl and hydroxyl groups in anti-fashion.

摘要

本报告概述了我们使用两种非羟醛缩合变体合成立体化学定义明确的酮，即 muamvatin 的 C-C 片段的努力，muamvatin 是第一个 2,4,6-三氧杂金刚烷环骨架聚丙酸盐海洋天然产物。i）Shimizu 反应，即 Pd(0) 介导的烯丙基环氧化物的立体选择性开环反应，用于以顺式方式立体选择性地安装甲基，ii）Bode 方案，即 NHC 介导的β-环氧醛的反应，用于以反式方式立体选择性地构建甲基和羟基。