Routes to Advanced Intermediates in the Synthesis of Tetracarbocyclic Sesquiterpenoids Daphnenoid A and Artatrovirenols A and B
Jiarui Zong,
Kirsten E. Christensen,
Jeremy Robertson
Abstract:A short route from
dihydrocarvone is described, which
led to the
tetracarbocyclic core common to artatrovirenol A and B and daphnenoid
A. A variant of this route afforded guaia-4,6-dien-3-one (from Enterospermum madagascarensis) and its epimer. From 2-(2-oxoethyl)furan,
a 15-step sequence then delivered the complete carbon skeleton and
all functionality necessary for daphnenoid A. Key steps in the route
include diastereoselective intramolecular oxidopyrylium cycloaddition,
oxa-bridge cleavage under “push–pull… Show more
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