Total synthesis of an enantiomeric pair of FR900482. 1. Synthetic and end-game strategies

Article abstract of DOI:10.1016/S0040-4020(97)00650-9

A synthetic strategy for an enantiomeric pair of FR900482 (1) was developed, which features a convergent and enantioselective sequence starting from 5-hydroxyisophthalic acid (16) and each enantiomer of diethyl tartrate (17 and ent-17). The proposed key intermediate 10 was synthesized from FK973 (3), the triacetyl derivative of 1, and successful reconversion of 10 into 1 was also achieved. These preliminary studies definitely demonstrated that 10 is suitable as a potential advanced key intermediate for 1 and that the crucial final sequence of reactions (10→1) involving delicate deprotection and oxidation steps can be realized.