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Stereoselective Synthesis of the C31–C41 Spirolactam Fragment of Sanglifehrin A
Author(s) -
Yadav J. S.,
Raghavendra Rao K. V.,
Kavita Aala,
Mohapatra Debendra K.
Publication year - 2013
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.201201684
Subject(s) - chemistry , stereoselectivity , desymmetrization , deoxygenation , stereochemistry , aldol reaction , organic chemistry , enantioselective synthesis , catalysis
A stereoselective synthesis of the spirolactam fragment (C31–C41) of a highly‐potent immunosuppressant sanglifehrin A is described. The key steps involved in this synthesis are a desymmetrization protocol, Sharpless asymmetric epoxidation, Crimmins syn aldol reaction, Barton–McCombie deoxygenation, and acid‐mediated spirolactamization.