A Convergent Synthesis of Carbocyclic Sinefungin and its C-5 Epimer.

A convergent synthesis of carbocyclic sinefungin ( 2), its C-5 epimer 3a, and adenine-modified derivative 3b is described. The key features of our approach include the use of commercially available L-methionine and readily available (1 R,4 S)-4-hydroxy-2-cyclopentenyl acetate as starting materials, a cross-metathesis reaction, an enzymatic kinetic resolution, and a Staudinger reduction. The current synthesis is flexible and, therefore, provides convenient access to the synthesis of various carbocyclic sinefungin analogues for biological evaluation. [ABSTRACT FROM AUTHOR]