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Asymmetric Total Synthesis of (+)-Spiroapplanatumine G
Yongqi Lin1, Freda F Li1,2, Margaret A Brimble1,2
1School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand.
Abstract:
Spiroapplanatumine G (7) is a spiro-meroterpenoid characterized by an unusual 6/5/7 tricyclic spirobenzofuran-3-one core. The first enantioselective total synthesis of spiroapplanatumine G (7) is reported, featuring a key enantioselective Diels-Alder reaction between an aurone ester and a silyloxydiene to assemble the spirobenzofuranone core. This strategic Diels-Alder transformation advantageously establishes the two contiguous stereogenic centers in a single step. Subsequent cyclopropanation/FeCl3-mediated oxidative ring expansion affords the desired tricyclic framework.
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