Open AccessEnantiospecific Entry to a Common Decalin Intermediate for the Syntheses of Highly Oxygenated Terpenoids
Author(s) -
Sumio Nagasawa,
Kerry E. Jones,
Richmond Sarpong
Publication year - 2019
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.9b01937
Subject(s) - decalin , chemistry , carvone , enantiomer , terpenoid , stereochemistry , olefin fiber , bicyclic molecule , monoterpene , combinatorial chemistry , organic chemistry , catalysis , limonene , chromatography , essential oil
Herein, we describe an enantiospecific route to one enantiomer of a common decalin core that is present in numerous highly oxygenated terpenoids. This intermediate is accessed in eight steps from ( R )-carvone, an inexpensive, enantioenriched building block, which can be elaborated to the desired bicycle through sequential Fe(III)-catalyzed reductive olefin coupling and Dieckmann condensation. The same synthetic route may be applied to ( S )-carvone to afford the enantiomer of this common intermediate for other applications.