Total Synthesis of (−)-Principinol C

We have achieved the first total synthesis of (−)-principinol C, which possesses an intriguing and complex 5/7/6/5 tetracyclic skeleton with eight contiguous stereocenters. The 5/7/6/5 tetracyclic skeleton of principinol C was assembled using an intramolecular Pauson–Khand reaction as the key step....

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Bibliographic Details
Published in:Journal of the American Chemical Society 2022-11, Vol.144 (44), p.20196-20200
Main Authors: Ma, Tianhao, Cheng, Hao, Pitchakuntla, Mallesham, Ma, Weihao, Jia, Yanxing
Format: Article
Language:English
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Summary:We have achieved the first total synthesis of (−)-principinol C, which possesses an intriguing and complex 5/7/6/5 tetracyclic skeleton with eight contiguous stereocenters. The 5/7/6/5 tetracyclic skeleton of principinol C was assembled using an intramolecular Pauson–Khand reaction as the key step. This synthetic route represents the first application of the intramolecular Pauson–Khand reaction of enyne to construct the 7,5-bicyclic ring system in natural product synthesis.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.2c08694