The Formal Total Synthesis of FR252921 – An Immunosuppressant. Issue 2 (15th November 2012)

• Record Type: Journal Article
• Authors: Yadav, J. S.; Sengupta, Sandip
• Is Part Of: European journal of organic chemistry. Issue 2(2013)
• Page Start: 376
• Page End: 388
• Publication Date: 2012-11-15
• Subjects: Total synthesis -- Natural products -- Macrocycles -- Kinetic resolution -- ­Alkylation -- Olefination; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201097
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 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.