The Formal Total Synthesis of FR252921 – An Immunosuppressant
European Journal of Organic Chemistry Volume 2013, Issue 2, pages 376–388, January 2013 J. S. Yadav and Sandip Sengupta
Article first published online: 15 NOV 2012 | DOI: 10.1002/ejoc.201201097
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.
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.
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