An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline, involving the kinetic resolution of racemic 1-(3-pyridyl)ethanol, the orthoester Claisen rearrangement of the enantiopure allylic alcohol 5, Smith indolization of the resulting 4-piperidineacetate 6, photocyclization of chloroacetamide 9, and final transannular cyclization, is reported. Copyright (C) 1996 Elsevier Science Ltd
An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline / M. Amat, M. Coll, D. Passarella, J. Bosch. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 7:10(1996), pp. 2775-2778. [10.1016/0957-4166(96)00359-X]
An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline
D. PassarellaPenultimo
;
1996
Abstract
An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline, involving the kinetic resolution of racemic 1-(3-pyridyl)ethanol, the orthoester Claisen rearrangement of the enantiopure allylic alcohol 5, Smith indolization of the resulting 4-piperidineacetate 6, photocyclization of chloroacetamide 9, and final transannular cyclization, is reported. Copyright (C) 1996 Elsevier Science Ltd
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