Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form
D-Scholarship @ Pitt Banner and Links to Homepage

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

[img] Plain Text (licence)
Available under License : See the attached license file.
Download (1kB)

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.

Share

Citation/Export:
Social Networking:
Share |

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-dev.library.pitt.edu/id/eprint/20548

Metrics

Monthly Views for the past 3 years

Plum Analytics

Altmetric.com

Actions (login required)

View Item View Item