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Total Syntheses of (+)‐Aquatolide and Related Humulanolides
Author(s) -
Takao Kenichi,
Kai Hirotaka,
Yamada Ai,
Fukushima Yuuki,
Komatsu Daisuke,
Ogura Akihiro,
Yoshida Keisuke
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201904404
Subject(s) - total synthesis , ring (chemistry) , chemistry , biomimetic synthesis , stereochemistry , combinatorial chemistry , organic chemistry
The short, efficient total synthesis of (+)‐aquatolide was achieved by a biomimetic transannular [2+2] photocycloaddition, and provides the first example of constructing a 5/5/4/8‐ring system from asteriscunolides. Furthermore, the reaction leading to a 5/4/4/7‐ring system, the originally proposed structure of aquatolide, was also developed. This strategy achieved syntheses of five more humulanolides, (−)‐asteriscunolides A, C, D, and I, and (+)‐tetradehydroasteriscanolide.
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