Synthesis of the bicyclic butenolide core of pallamolide A: a biomimetic approach†
Grace J.
Drummond, 
a
Phillip S.
Grant,
a
Alisha M.
Geurts,
a
Daniel P.
Furkert
ab
and
Margaret A.
Brimble
*ab
a
Phillip S.
Grant,
a
Alisha M.
Geurts,
a
Daniel P.
Furkert
ab
and
Margaret A.
Brimble
*ab
Abstract
Pallamolide A is a 7,8-seco-labdane terpenoid possessing a unique bicyclo[2.2.2]octane core and a spiro-butenolide moiety. A biomimetic synthesis of the bicyclic butenolide core over 10 steps is reported, featuring an unexpected autoxidation ring opening, and a vinylogous Mukaiyama aldol reaction which was spontaneously followed by an unusual intramolecular vinylogous aldol reaction to assemble the spiro-butenolide moiety and bicyclic core of pallamolide A.
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