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Diastereoselective Total Synthesis of (±)‐Toxicodenane A
Author(s) -
Kobayashi Toyoharu,
Yamanoue Kotono,
Abe Hideki,
Ito Hisanaka
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701219
Subject(s) - chemistry , desymmetrization , total synthesis , dimedone , moiety , bicyclic molecule , metathesis , epoxide , stereochemistry , ring (chemistry) , diene , sesquiterpene , salt metathesis reaction , yield (engineering) , enantioselective synthesis , organic chemistry , catalysis , polymer , natural rubber , materials science , metallurgy , polymerization
The first total synthesis of tricyclic sesquiterpene (±)‐toxicodenane A has been accomplished. This synthetic work was completed in 12 steps from dimedone through diastereoselective reductive desymmetrization of 2,2‐disubstituted 5,5‐dimethylcyclohexane‐1,3‐dione, stereocontrolled allylation, ring‐closing metathesis of a diene compound to yield bicyclic compounds that bear a seven‐membered ring, and construction of the oxygen‐bridged moiety through neighboring group assisted ring‐opening reaction of an epoxide as key steps.