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Total syntheses of the Strychnos indole alkaloids(−)-tubifoline, (−)-tubifolidine, and (−)-19,20-dihydroakuammicine

✍ Scribed by Mercedes Amat; M.-Dolors Coll; Joan Bosch; Enric Espinosa; Elies Molins

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 1017 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00071-2

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✦ Synopsis

Two different strategies for the synthesis of pentacyclic Strychnos alkaloids in enantiomerically pure form are explored. Both of them involve the use of enantiopure 2-(4-piperidylmethyl)indoles prepared by kinetic resolution of l-(3-pyridyl)ethanol, followed by partial reduction of the pyridine ring to the tetrahydropyridine level, Claisen rearrangement of the resulting allylic alcohol, and finally Smith indolization. Whereas 2-(4-piperidylmethyl)indole 6 could not be converted to tetracyclic ABDE substructures of Strychnos alkaloids, photocyclization of chloroacetamide 14, derived from (piperidylmethyl)indole 13, satisfactorily afforded the stemmadenine-type tetracycle 15, which was then converted to the alkaloids (-)-tubifoline, (-)-tubifolidine, and (-)-19,20dihydroakuammicine. (~)

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