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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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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]
Total Authors: 7
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
Total Affiliations: 3
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