Stereoselective total synthesis of (S)- and (R)-nuciferine using benzyne chemistry

Author(s)

Perecim, Givago P. ^[1] ; Deflon, Victor M. ^[2] ; Martins, Gabriel R. ^[3] ; Pinto, Leandro M. C. ^[3] ; Casagrande, Gleison A. ^[3] ; Oliveira-Silva, Diogo ^[1] ; Raminelli, Cristiano ^[1]

Affiliation

^[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Rua Prof Artur Riedel 275, BR-09972270 Diadema, SP - Brazil

^[2] Univ Sao Paulo, Inst Quim Sao Carlos, Av Trabalhador Sao Carlense 400, BR-13566590 Sao Carlos, SP - Brazil

^[3] Univ Fed Mato Grosso Do Sul, Inst Quim, Av Senador Filinto Muller 1555, BR-79074460 Campo Grande, MS - Brazil

• Document type: Journal article
• Source: Tetrahedron; v. 76, n. 38 SEP 18 2020.
• Web of Science Citations: 0

Abstract

Total syntheses of (S)- and (R)-nuciferine were accomplished through approach involving diastereoselective reaction between a chiral dihydroisoquinoline enamide and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate promoted by CsF, affording a separable mixture of diastereoisomers, which provided (S)- and (R)-nuciferine via simple and efficient transformations. (C) 2020 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 09/54011-8 - Acquisition of a single-crystal X-ray diffractometer for the structural analysis of small molecules and proteins
• Grantee: Victor Marcelo Deflon
• Support Opportunities: Multi-user Equipment Program
• FAPESP's process: 17/21990-0 - 2-(Trialkylsilyl)aryl trifluoromethanesulfonates as aryne precursors in the development of methodologies for obtaining nitrogen-containing heterocyclic compounds and total syntheses of bioactive natural products
• Grantee: Cristiano Raminelli
• Support Opportunities: Regular Research Grants