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Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol
Author(s) -
Xu Bo,
Xun Wen,
Su Shaobin,
Zhai Hongbin
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007247
Subject(s) - stereocenter , annulation , alkene , nitrile , stereochemistry , total synthesis , chemistry , enantioselective synthesis , organic chemistry , catalysis
Cyclopianes are novel diterpenes featuring a highly strained 6/5/5/5 tetracyclic core embedded with 6–8 consecutive stereocenters. The concise total syntheses of (−)‐conidiogenone B, (−)‐conidiogenone, and (−)‐conidiogenol have been accomplished in 14–17 steps. The present work features a HAT‐mediated alkene–nitrile cyclization to access the cis ‐biquinane, a Nicholas/Pauson–Khand reaction to construct the linear triquinane, and a Danheiser annulation to afford the congested angular triquinane skeleton.