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The Formal Total Synthesis of FR252921 – An Immunosuppressant
Author(s) -
Yadav J. S.,
Sengupta Sandip
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.201201097
Subject(s) - chemistry , stereocenter , allene , moiety , stereochemistry , isomerization , enyne , total synthesis , formal synthesis , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
The formal total synthesis of FR252921 is described. The key steps include the preparation of three fragments starting from 1,4‐butanediol, ( R )‐malic acid, and prenol, respectively, followed by two consecutive peptide couplings of the three fragments. Other key steps involve an allene‐type rearrangement or enyne isomerization to install the triene moiety, a Seebach methylation, a Julia olefination to construct the trisubstituted diene unit, and an enzymatic resolution strategy to generate the C‐18 stereocenter.