Work

A Convergent Synthesis of Carbocyclic Sinefungin and its C‐5 Epimer

Year: 2014

Type: article

Abstract: 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 (1R,4S)‐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.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.201402812

Authors: Arun K. Ghosh, Kai Lv

Institution: Purdue University West Lafayette

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Purdue University Center for Cancer Research, National Institutes of Health, National Institute of General Medical Sciences, National Institute of Allergy and Infectious Diseases

Awards: Inhibition and mechanism of flavivirus methyltransferase, Design & Synthesis of Nonpeptide Protease Inhibitors