Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (+/-)-stemoamide and its 9a-epimer

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Author(s):	Brito, Gilmar A. ^[1] ; Sarotti, Ariel M. ^[2] ; Wipf, Peter ^[3] ; Pilli, Ronaldo A. ^[1] Total Authors: 4
Affiliation:	^[1] Univ Campinas Unicamp, Inst Chem, BR-13084971 Campinas, SP - Brazil ^[2] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario CONICET, RA-2000 Rosario, Santa Fe - Argentina ^[3] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 - USA Total Affiliations: 3
Document type:	Journal article
Source:	Tetrahedron Letters; v. 56, n. 48, p. 6664-6668, DEC 2 2015.
Web of Science Citations:	5
Abstract
A concise formal synthesis of stemoamide (1) and its 9a-epimer 14 in 5 steps is described featuring a cascade cyclization triggered by imine formation. A good selectivity for either epimer is readily accomplished by variation of the ester (9b or 9a, respectively) and the reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved. (AU)

FAPESP's process:	09/51602-5 - Chemical biology: new natural and synthetic molecular targets against cancer, structural studies, biological evaluation and mode of action
Grantee:	Ronaldo Aloise Pilli
Support Opportunities:	Research Projects - Thematic Grants


FAPESP's process:	10/00219-4 - Asymmetric synthesis and structural determination of (-)-parviestemoamide.
Grantee:	Gilmar Araujo Brito Junior
Support Opportunities:	Scholarships in Brazil - Doctorate