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https://hdl.handle.net/2440/122474
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Type: | Journal article |
Title: | Total synthesis of naphterpin and marinone natural products |
Author: | Murray, L.A.M. Fallon, T. Sumby, C.J. George, J.H. |
Citation: | Organic Letters, 2019; 21(20):8312-8315 |
Publisher: | ACS Publications |
Issue Date: | 2019 |
ISSN: | 1523-7060 1523-7052 |
Statement of Responsibility: | Lauren A. M. Murray, Thomas Fallon, Christopher J. Sumby, and Jonathan H. George |
Abstract: | A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6π-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone. |
Keywords: | Naphthoquinones Biological Products Molecular Structure Stereoisomerism |
Rights: | Copyright © 2019 American Chemical Society |
DOI: | 10.1021/acs.orglett.9b03095 |
Grant ID: | http://purl.org/au-research/grants/arc/FT170100437 |
Published version: | http://dx.doi.org/10.1021/acs.orglett.9b03095 |
Appears in Collections: | Aurora harvest 8 Chemistry publications |
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