Chemical Communications 2013-03-07

Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline.

Mercedes Amat, Carlos Ramos, Maria Pérez, Elies Molins, Pedro Florindo, Maria M M Santos, Joan Bosch

Index: Chem. Commun. (Camb.) 49(19) , 1954-6, (2013)

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Abstract

Starting from (S)-tryptophanol, a formal synthesis of ent-rhynchophylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.