Biomimetic and Biocatalytic Synthesis of Bruceol.
Angew Chem Int Ed Engl
; 58(5): 1427-1431, 2019 01 28.
Article
em En
| MEDLINE
| ID: mdl-30548759
ABSTRACT
The first total synthesis of bruceol has been achieved using a biomimetic cascade cyclization initiated by a stereoselective Jacobsen-Katsuki epoxidation (and kinetic resolution) of racemic protobruceol-I. A bacterial cytochrome P450 monooxygenase was also found to catalyze the conversion of protobruceol-I into bruceol. The first full analysis of the NMR data of natural bruceol suggested that "isobruceol" was a previously unrecognized natural product also isolated from Philotheca brucei. This was confirmed by the re-isolation, synthesis, and X-ray analysis of isobruceol. In total, eight stereoisomers and structural isomers of bruceol have been synthesized in a highly divergent approach.
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Base de dados:
MEDLINE
Assunto principal:
Terpenos
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Produtos Biológicos
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Sistema Enzimático do Citocromo P-450
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Materiais Biomiméticos
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Compostos Heterocíclicos de 4 ou mais Anéis
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Austrália