Stereoselective Synthesis of the Side Chains of Mycolactones A and B Featuring Stepwise Double Substitutions of l,l-Dibromo-l-alkenes

摘要

We report herein a Stereoselective synthesis of the side chains of mycolactones A (1A) and B (1B).These side chains 2A and 2B,respectively,are protected as a methoxymethyl (MOM) ether at C12 and tert-butyldimethylsilyl (TBS) derivatives at C13 and C15,and are thus ready to be used as intermediates for the synthesis of 1A and 1B (Scheme 1).Mycolactones A (1A) and B (1B) were isolated in 1999 by Small and co-workers from Mycobacterium ulcerans,the causative pathogen of Buruli ulcer.