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Total Synthesis of (−)-Bafilomycin A1: Application of Diastereoselective Crotylboration and Methyl Ketone Aldol Reactions
Article first published online: 26 MAY 1999
DOI: 10.1002/(SICI)1521-3773(19990601)38:11<1652::AID-ANIE1652>3.0.CO;2-K
© 1999 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany
1521-3773(19990601)38:11<>1.0.CO;2-%23/asset/cover.gif?v=1&s=cf7cd76ba1cdb2a534f6f32814729776ef219d5b "Angewandte Chemie International Edition")
Additional Information
How to Cite
Scheidt, K. A., Tasaka, A., Bannister, T. D., Wendt, M. D. and Roush, W. R. (1999), Total Synthesis of (−)-Bafilomycin A1: Application of Diastereoselective Crotylboration and Methyl Ketone Aldol Reactions. Angewandte Chemie International Edition, 38: 1652–1655. doi: 10.1002/(SICI)1521-3773(19990601)38:11<1652::AID-ANIE1652>3.0.CO;2-K
Publication History
- Issue published online: 26 MAY 1999
- Article first published online: 26 MAY 1999
- Manuscript Received: 10 DEC 1998
- Abstract
- Cited By
Keywords:
- Aldol reactions;
- Asymmetric synthesis;
- Bafilomycin;
- Total synthesis
Abstract
A careful orchestration of protecting groups is an essential requirement for the total synthesis of the macrolide antibiotic bafilomycin A1 (1). Key steps were the Suzuki cross-coupling reaction of two advanced, suitably protected intermediates prior to closure of the macrocycle, as well as a highly stereoselective methyl ketone aldol reaction.