Total synthesis of phomactin B2

ORGN 700

Chunrui Wu, wuchunru@msu.edu, Jie Huang, huangj@cem.msu.edu, and William D. Wulff, wulff@chemistry.msu.edu. Department of Chemistry, Michigan State University, East Lansing, MI 48823
Phomactin B2, isolated from the marine fungus Phoma sp., demonstrated biological activity as PAF antagonist . Our strategy to synthesize this natural product involved the intramolecular cyclohexadinenone annulation of Fischer carbene complex (1) to construct the highly substituted macrocycle (2) as the key intermediate. Subsequent Peterson Olefination, methylation gave a full carbon skeleton, which was further modified to provide both phomactin B2 and its C13 -epimer.