The Formal Total Synthesis of FR252921 - An Immunosuppressant

Yadav, J. S. ; Sengupta, Sandip (2012) The Formal Total Synthesis of FR252921 - An Immunosuppressant European Journal of Organic Chemistry, 2013 (2). pp. 376-388. ISSN 1434-193X

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Official URL: http://doi.org/10.1002/Ejoc.201201097

Related URL: http://dx.doi.org/10.1002/Ejoc.201201097

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.

Item Type:Article
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ID Code:135760
Deposited On:14 Aug 2023 09:16
Last Modified:14 Aug 2023 09:16

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