The acyclic dienamine-indoloacrylate addition route to catharanthine |
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| Authors: | Nan Huang Tiansheng Wang Mustapha Soukri Rakesh Ganorkar Bruce Deker Jose Madalengoitia |
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| Institution: | a Department of Chemistry, University of Vermont, Burlington, VT 05405, United States
b EA 2962, Pharmacochimie, Université Victor Segalen, 146 Rue Léo Saignat, 33076, Bordeaux II, Cedex, France |
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| Abstract: | Condensation of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino4,5-b]indole-5-carboxylate (3) with methyl Z-4-formylhex-3-enoate (6) gave cis-fused dimethyl 5-benzyl-4-ethyl-2,4a,5,6,7,12-hexahydro-1H-benzo2,3]azepino4,5-b]indole-2,12b-dicarboxylate and its trans-fused diastereomer. Selective reduction of the less hindered ester group with sodium borohydride to an alcohol ester, tosylation, debenzylation, and cyclization gave racemic catharanthine (1). |
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| Keywords: | Indole alkaloids Catharanthine synthesis |
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