A Highly Convergent Total Synthesis of (+)‐Myxovirescine M 2 . Preliminary Communication

The antibiotic myxovirescine M 2 was synthesized from seven building blocks ( 1 – 7 , Scheme 1 ), with the following chiral starting materials being employed: ( S )‐malic acid, (+)‐ D ‐ribonolactone, ( S )‐2‐(hydroxymethyl)butanoate, and (2 R ,4 S )‐5‐hydroxy‐2,4‐dimethylpenLanoate. Three new nucleophilic reagents, 8 – 10 , for C‐C bond formation have been used. The key steps of the synthesis are: a Suzuki coupling between an alkyl borane and a vinyl bromide ( 4 + 12e → 13 ), a Julia olefinalion ( 14 + 17 → 18 ), and a Yamaguchi macrolactonizalion to form the 28‐membered lactone ( 18 → 19 ), This extremely convergenl synthetic approach will allow the preparation of a number of the 31 known myxovirescine molecules.