DIVERGENT SYNTHESIS OF LAMELLARIN α 13-SULFATE, 20-SULFATE, and 13,20-DISULFATE

摘要

A divergent synthesis of three sulfate derivatives of lamellarin a, namely, lamellarin α 13-sulfate (2), 20-sulfate (1), and 13,20-disulfate (4) has been achieved via a common intermediate (6) in which 13-OH and 20-OH of the Jamellarin core are differentially protected by MOM and benzyl groups, respectively. Compound (6) in turn was prepared using sequential Suzuki-Miyaura coupling of 3,4-dihydroxypyrrole bistriflate (7) as a key reaction.