title: A convergent synthesis of carbocyclic sinefungin and its C5 epimer.
abstract: A convergent synthesis of carbocyclic sinefungin2and its C5 epimer3is described. The key features in our synthesis include the use of commercial available L-methionine and readily available (1R, 4S)-4-hydroxy-2-cyclopentenyl acetate as starting materials, cross-metathesis coupling, enzymatic kinetic resolution and Staudinger reduction. The current synthesis is flexible and therefore provides convenient access to the synthesis of various carbocyclic SIN analogues for biological evaluation.
authors.affiliation: Department of Chemistry and Department of Medicinal Chemistry, Purdue University, West Lafayette, Indiana, 47906 (USA).
authors.forename: Arun K
authors.initials: AK
authors.lastname: Ghosh
authors.affiliation: Department of Chemistry and Department of Medicinal Chemistry, Purdue University, West Lafayette, Indiana, 47906 (USA).
authors.forename: Kai
authors.initials: K
authors.lastname: Lv
keywords: carbocyclic derivative; enzyme resolution; methyltransferase; sinefungin; synthesis