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Studies directed toward the total synthesis of 14-membered cyclopeptide alkaloids: Synthesis of a cyclic precursor to nummularine-F

✍ Scribed by Robert J. Heffner; Madeleine M. Joullié

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
289 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

A highiy strained Il-memberedpara-ansa cyclopeptide, a potentialprecursor of the cyclopeptide alkaloid, nummularine-F, was made by cyclization of a pentafluorophenyl ester under catalytic hydrogenation conditions. This cyciization and the stereoselective synthesis of the acyclic activated ester f/am D-set&, are presented. Since 1966, when the structure of pandamine was confiied,l more than 100 cyclopeptide alkaloids have been isolated and their structures elucidated. Cyclopeptide alkaloids are particularly common in plants of the Rhamnacea family, and have also been discovered in more than 25 other species of plants. Their widespread oc-(

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