Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/137371
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Type: | Journal article |
Title: | A bioinspired, one-step total synthesis of peshawaraquinone |
Author: | Vieira de Castro, T. Huang, D.M. Sumby, C.J. Lawrence, A.L. George, J.H. |
Citation: | Chemical Science, 2023; 14(4):950-954 |
Publisher: | Royal Society of Chemistry (RSC) |
Issue Date: | 2023 |
ISSN: | 2041-6520 2041-6539 |
Statement of Responsibility: | Tomas Vieira de Castro, David M. Huang, Christopher J. Sumby, Andrew L. Lawrence and Jonathan H. George |
Abstract: | A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, via the unsymmetrical dimerization of its achiral precursor, dehydro-a-lapachone, is reported. Enabled by reversible oxa-6p-electrocyclizations of 2H-pyran intermediates, the base-catalyzed dimerization sets up an intramolecular (3 + 2) cycloaddition, with the formation of six stereocenters during the cascade. Combining the generation and in situ dimerization of dehydro-a-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal. |
Rights: | © 2023 The Author(s). Published by the Royal Society of Chemistry. Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. |
DOI: | 10.1039/d2sc05377b |
Grant ID: | http://purl.org/au-research/grants/arc/DP200102964 http://purl.org/au-research/grants/arc/LE210100163 |
Published version: | http://dx.doi.org/10.1039/d2sc05377b |
Appears in Collections: | Chemistry publications |
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hdl_137371.pdf | Published version | 668.95 kB | Adobe PDF | View/Open |
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