Progress toward the total synthesis of bryostatin 1: Emphasis on C17-C27 fragment

ORGN 729

Victoria L Wilde, vlwilde@wisc.edu and Steven D. Burke, burke@chem.wisc.edu. Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706
The bryostatins are a family of 20-membered ring macrolides, which exhibit antitumor activity. Each of the bryostatins are made up of three highly substituted tetrahydropyran rings. The C17-C27 fragment, compound 1, of bryostatin 1 is quickly and efficiently synthesized via DIBAl-H/Horner-Wadsworth-Emmons coupling and acetonide migration/glycal formation cascade. The fully elaborated core, compound 2, is completed in only 12 linear steps (15 total steps) from (R)-2-(benzyloxy)propanal. Progress toward the coupling of the northern and southern hemispheres of bryostatin 1 as well as the development of a new coupling strategy will be discussed.