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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202104182
Subject(s) - enantioselective synthesis , chemistry , total synthesis , vinyl bromide , bromide , ring (chemistry) , octane , combinatorial chemistry , stereochemistry , catalysis , organic chemistry
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.