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A Convergent Synthesis of Carbocyclic Sinefungin and its C‐5 Epimer
Author(s) -
Ghosh Arun K.,
Lv Kai
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402812
Subject(s) - epimer , chemistry , stereochemistry , metathesis , convergent synthesis , kinetic resolution , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , polymerization , polymer
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.