Issue 15, 2006
From the journal:

Organic & Biomolecular Chemistry

The dihydrofuran template approach to furofuran synthesis†

David J. Aldous,b   Andrei S. Batsanov,a   Dmitrii S. Yufit,a   Anne J. Dalençon,a   William M. Duttona  and  Patrick G. Steel*a  

* Corresponding authors

a Department of Chemistry, University of Durham, South Road, Durham, UK
E-mail: p.g.steel@durham.ac.uk
Fax: +44-(0)191-384-4737
Tel: +44-(0)191-334-2131

b Sanofi-Aventis Pharma Inc, Route 202-206, Bridgewater, P.O. Box 6800, New Jersey 08807, USA

Abstract

Flash vacuum pyrrolysis of vinyl epoxides provides cis-dihydrofuran carboxylic esters in good yields and diastereoselectivities, which, on base-promoted epimerisation afford the complementary trans series. The compounds provide a viable template for a Lewis acid promoted cyclisation to provide the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in the furofuran series of natural lignans. This strategy is stereodivergent and can be controlled to provide the exo-exo, exo-endo or endo-endo stereochemistries. The approach has been exemplified in syntheses of the sesamyl furofurans (±)-epiasarinin and (±)-asarinin.

Graphical abstract: The dihydrofuran template approach to furofuran synthesis

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B604952D
Article type
Paper
Submitted
06 Apr 2006
Accepted
30 May 2006
First published
30 Jun 2006

Org. Biomol. Chem., 2006,4, 2912-2927

Permissions

Request permissions

The dihydrofuran template approach to furofuran synthesis

D. J. Aldous, A. S. Batsanov, D. S. Yufit, A. J. Dalençon, W. M. Dutton and P. G. Steel, Org. Biomol. Chem., 2006, 4, 2912 DOI: 10.1039/B604952D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements