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A concise, selective synthesis of the polyketide spacer domain of a potent bryostatin analogue
Paul A Wender1, Alexander V W Mayweg, Christopher L VanDeusen
1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@leland.stanord.edu
Abstract:
[reaction: see text] A concise, asymmetric synthesis of the polyketide spacer domain portion (C1-C13) of a highly potent bryostatin analogue was developed. The route utilizes asymmetric hydrogenation methodology to install the C3, C5, and C11 stereocenters, while a substrate directed syn reduction sets the C9 stereocenter. The spacer domain 1 is obtained in 10 steps with a 25% overall yield and is readily incorporated into the synthesis of 2.
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