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A convergent synthesis of carbocyclic sinefungin and its C5 epimer.

ABSTRACT: A convergent synthesis of carbocyclic sinefungin 2 and its C5 epimer 3 is 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.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC4267295 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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A convergent synthesis of carbocyclic sinefungin and its C5 epimer.

Ghosh Arun K AK Lv Kai K

European journal of organic chemistry 20141001 30

A convergent synthesis of carbocyclic sinefungin 2 and its C5 epimer 3 is 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 f ...[more]

PMID: 25530707

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