Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol | Zendy

Xu Bo | Zendy; Xun Wen | Zendy; Su Shaobin | Zendy; Zhai Hongbin | Zendy

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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.

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