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Total Syntheses of Norrisolide‐Type Spongian Diterpenes Cheloviolene C, Seconorrisolide B, and Seconorrisolide C
Author(s) -
Qiao Tianjiao,
Wang Yicheng,
Zheng Sujuan,
Kang Huiying,
Liang Guangxin
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202005600
Subject(s) - furan , stereochemistry , intramolecular force , total synthesis , chemistry , ring (chemistry) , stereoselectivity , diterpene , organic chemistry , catalysis
The first total syntheses of three unusual norrisolide‐type rearranged spongian diterpenes, cheloviolene C, seconorrisolide B, and seconorrisolide C, have been accomplished via a common intermediate through late‐stage ring‐scissoring. The synthesis features a Wolff ring contraction for the synthesis of the trans‐hydrindane system, and a crucial retro Diels–Alder reaction/intramolecular ene cyclization for the rapid stereoselective construction of the furo[2,3‐b]furan system, which is commonly seen in rearranged spongian diterpenes.