Premium
Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C
Author(s) -
Zong Yan,
Xu ZeJun,
Zhu RongXiu,
Su AiHong,
Liu XuYuan,
Zhu MingZhu,
Han JingJing,
Zhang JiaoZhen,
Xu YuLiang,
Lou HongXiang
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202104182
Subject(s) - enantioselective synthesis , chemistry , vinyl bromide , total synthesis , ring (chemistry) , bromide , octane , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
An enantioselective synthetic approach for preparing manginoids and guignardones, two types of biogenetically related meroterpenoids, is reported. This bioinspired and divergent synthesis employs an oxidative 1,3‐dicarbonyl radical‐initiated cyclization and cyclodehydration of the common precursor to forge the central ring of the manginoids and guignardones, respectively, at a late stage. Key synthetic steps include silica‐gel‐promoted semipinacol rearrangement to form the 6‐oxabicyclo[3.2.1]octane skeleton and the Suzuki–Miyaura reaction of vinyl bromide to achieve fragment coupling. This synthesis protocol enables the asymmetric syntheses of four fungal meroterpenoids from commercially available materials.