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Total synthesis of (+/-)-bipinnatin J
1Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Organic Letters
|January 27, 2006
Abstract:
[reaction: see text]. The total synthesis of (+/-)-bipinnatin J was achieved through a concise route that features the use of a silver ion promoted S(N)1-type gamma-alkylation of a siloxyfuran and a diastereoselective Cr(II)-mediated macrocyclization to provide bipinnatin J (1), wherein the remote furanone stereocenter at C10 induced the relative stereochemistry of the two additional stereocenters.
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