Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/119444
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Type: Journal article
Title: Biomimetic and biocatalytic synthesis of bruceol
Author: Day, A.
Lee, J.
Phan, Q.D.
Lam, H.
Ametovski, A.
Sumby, C.
Bell, S.
George, J.
Citation: Angewandte Chemie - International Edition, 2019; 58(5):1427-1431
Publisher: Wiley
Issue Date: 2019
ISSN: 1433-7851
1521-3773
Statement of
Responsibility: 
Aaron J. Day, Joel H. Z. Lee, Quang D. Phan, Dr. Hiu C. Lam, Adam Ametovski, Christopher J. Sumby, Stephen G. Bell, Jonathan H. George
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.
Keywords: biomimetic synthesis; biosynthesis; cascade reactions; natural products; total synthesis
Rights: © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
RMID: 0030105744
DOI: 10.1002/anie.201812432
Grant ID: http://purl.org/au-research/grants/arc/FT170100437
http://purl.org/au-research/grants/arc/FT140100355
Appears in Collections:Chemistry publications

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