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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.)

Total synthesis of cryptomoscatones D1 and D2: stereochemical assignment of cryptomoscatone D1

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Author(s):
Toneto Novaes, Luiz Fernando [1] ; Drekener, Roberta Lopes [1] ; Avila, Carolina Martins [1] ; Pilli, Ronaldo Aloise [1]
Total Authors: 4
Affiliation:
[1] Univ Estadual Campinas, Dept Organ Chem, Inst Chem, Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Tetrahedron; v. 70, n. 37, p. 6467-6473, SEP 16 2014.
Web of Science Citations: 18
Abstract

The first total synthesis and structural elucidation of cryptomoscatone D1, and a novel synthetic approach for cryptomoscatone D2 were achieved in 30% and 29% overall yield, respectively. The synthesis relied on the use of a key Mukaiyama aldol reaction followed by a diastereoselective carbonyl reduction that allowed the preparation of four cryptomoscatone isomers in a stereochemically divergent manner. Comparison of NMR data and CD curves of the synthetic stereoisomers and natural products confirmed the stereochemical nature of cryptomoscatone D2, and led to establishing the absolute configuration of cryptomoscatone D1. (C) 2014 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 type: Research Projects - Thematic Grants