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Formal total synthesis of (+)-diepoxin σ

Wipf, P and Jung, JK (2000) Formal total synthesis of (+)-diepoxin σ. Journal of Organic Chemistry, 65 (20). 6319 - 6337. ISSN 0022-3263

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Abstract

The highly oxygenated antifungal anticancer natural product (±)-diepoxin σ was prepared in 10 steps and in 15% overall yield from O-methylnaphthazarin. Highlights of the synthetic work include an Ullmann coupling and a possibly biomimetic oxidative spirocyclization for the introduction of the naphthalene ketal as well as the use of a retro-Diels-Alder reaction to unmask the reactive enone moiety in the naphthoquinone bisepoxide ring system. A novel highly bulky chiral binaphthol ligand was developed for a boron-mediated Diels-Alder reaction that constitutes a formal asymmetric total synthesis of (+)-diepoxin σ.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Jung, JK
Date: 6 October 2000
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 65
Number: 20
Page Range: 6319 - 6337
DOI or Unique Handle: 10.1021/jo000684t
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Africa; Crystallography, X-Ray; Epoxy Compounds--chemical synthesis; Plants, Medicinal--chemistry; Spiro Compounds--chemical synthesis
Other ID: 10.1021/jo000684t
PubMed ID: 11052073
Date Deposited: 21 Feb 2014 21:08
Last Modified: 02 Feb 2019 15:56
URI: http://d-scholarship.pitt.edu/id/eprint/20548

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