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A Concise Total Synthesis of (±)‐Vibralactone
Author(s) -
Nistanaki Sepand K.,
Boralsky Luke A.,
Pan Roy D.,
Nelson Hosea M.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812711
Subject(s) - stereocenter , total synthesis , natural product , cyclopropanation , chemistry , isomerization , lactone , bicyclic molecule , stereochemistry , biomimetic synthesis , ring (chemistry) , terpenoid , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis
Disclosed is a five‐step synthesis of (±)‐vibralactone, a biologically active terpenoid natural product. A key photochemical valence isomerization of 3‐prenyl‐pyran‐2‐one produces both the all‐carbon quaternary stereocenter and the β‐lactone at an early stage. Cyclopropanation of the resulting bicyclic β‐lactone produces a strained housane structure that is converted to the natural product through a sequential ring expansion and reduction strategy. This concise and modular route to the natural product provides the shortest total synthesis of (±)‐vibralactone reported to date.