TOTAL SYNTHESIS OF AN ENANTIOMERIC PAIR OF FR900482 .1. SYNTHETIC AND END-GAME STRATEGIES

摘要

A synthetic strategy for an enantiomeric pair of FR900482 (1) was developed, which features a convergent and enantioselective sequence starling 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 mid that the crucial final sequence of reactions (10-->1) involving delicate deprotection and oxidation steps can be realised. (C) 1997 Elsevier Science Ltd. [References: 46]