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Total synthesis of virgatolide B
Paul A Hume1, Daniel P Furkert, Margaret A Brimble
1School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand.
Abstract:
The first total synthesis of the benzannulated spiroketal virgatolide A is presented. Key features include sp(3)-sp(2) Suzuki coupling of an enantiomerically enriched β-trifluoroboratoamide and an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction followed by global deprotection/cyclization with regioselectivity governed by internal hydrogen bonding.
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