Studies Toward the Stereoselective Synthesis of C13 to C21 Fragment of the Brasilinolides Family of Immunosuppressive Macrolides

Abstract

The work describes our attempts to synthesize the C13 to C21 fragment of brasilinolides, a 32-membered macrolide class of molecule. The C13 to C21 segment encompasses six asymmetric centers and a pyran ketal moiety. The synthesis starts from L-malic acid, and the salient features of our asymmetric synthesis are opening of epoxide, assymmetric dihydroxylation for the creation of vic-diol, and Barbier allylation.

GRAPHICAL ABSTRACT

Keywords:

• Asymmetric dihydroxylation
• Barbier allylation
• α/β-unsaturated ketone
• vic-diol