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Studies toward a synthesis of C3-epimauritine D: construction of the macrocycle

✍ Scribed by Young-Ah Kim; Hyo-Nim Shin; Myoung-Soon Park; So-Hye Cho; So-Yeop Han

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 216 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00278-8

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✦ Synopsis

We successfully synthesized a 14-membered cyclic enamide of C3-epimauritine D from the cis-2,3-pyrrolidinediol derivative. Treatment of the pyrrolidinediol with nitrobenzonitrile in an S N Ar reaction efficiently installed the desired aryl-alkyl ether linkage on the N-heterocyclic system. Macrocyclization was successfully achieved by the use of TFFH as the peptide coupling reagent in the presence of HOAt.

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