Total Synthesis of (-)-Bafilomycin A1 : Application of Diastereoselective Crotylboration and Methyl Ketone Aldol Reactions

Karl A Scheidt; Akihiro Tasaka; Thomas D Bannister; Michael D Wendt; William R Roush

doi:10.1002/(SICI)1521-3773(19990601)38:11<1652::AID-ANIE1652>3.0.CO;2-K

Total Synthesis of (-)-Bafilomycin A₁ : Application of Diastereoselective Crotylboration and Methyl Ketone Aldol Reactions

Angew Chem Int Ed Engl. 1999 Jun 1;38(11):1652-1655. doi: 10.1002/(SICI)1521-3773(19990601)38:11<1652::AID-ANIE1652>3.0.CO;2-K.

Authors

Karl A Scheidt¹, Akihiro Tasaka¹, Thomas D Bannister¹, Michael D Wendt¹, William R Roush¹

Affiliation

¹ Department of Chemistry, University of Michigan, Ann Arbor, MI, 48109 (USA), Fax: (+1) 734-647-9279.

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.

Keywords: Aldol reactions; Asymmetric synthesis; Bafilomycin; Total synthesis.