利用可见光促进的自由基环化反应合成马代罗内酯A的C13 - C27片段

Synthesis of the C13-C27 Fragment of Madeirolide A Using Visible-Light-Promoted Radical Cyclization.

作者信息

Hwang Sunghyun, Choi Minchul, Jeong Myungeun, Lee Chulbom

机构信息

Department of Chemistry, Seoul National University, Seoul 08826, Republic of Korea.

出版信息

Org Lett. 2024 Feb 9;26(5):1067-1072. doi: 10.1021/acs.orglett.3c04305. Epub 2024 Jan 31.

DOI:10.1021/acs.orglett.3c04305

PMID:38293710

Abstract

The convergent synthesis of a fully elaborated C13-C27 fragment of madeirolide A has been achieved. The key features of the synthesis include the stereocontrolled construction of both the THF and THP rings via visible-light-induced iridium-catalyzed radical cyclization and the late-stage union of the two oxacyclic subunits through nickel-catalyzed decarboxylative cross-coupling.

摘要

已实现了对马代罗内酯A中一个完全精细的C13 - C27片段的汇聚合成。该合成的关键特征包括通过可见光诱导的铱催化自由基环化对四氢呋喃（THF）环和四氢吡喃（THP）环进行立体控制构建，以及通过镍催化的脱羧交叉偶联实现两个含氧杂环亚基的后期结合。