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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
Statement of
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
Rights: Copyright © 2019 American Chemical Society
DOI: 10.1021/acs.orglett.9b03095
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