Issue 9, 2011
From the journal:

Organic & Biomolecular Chemistry

Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids†

Allan Patrick G. Macabeo,a   Andreas Kreuzera  and  Oliver Reiser*a  

* Corresponding authors

a Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, Regensburg, Germany
E-mail: Oliver.Reiser@chemie.uni-regensburg.de
Fax: +49 9419434621
Tel: +49 9419434631

Abstract

Titanium chelate addition of aryl nucleophiles to cyclopropyl aldehyde 6 followed by a tin-catalyzed one-pot retro-aldol, acetalisation and lactonisation sequence afforded cis and trans γ-aryllactone acetals. A γ-furyllactone derived by this approach was further transformed in two steps to model compounds for the oxidised northeastern sectors of selected Pseudopterogorgia diterpenoids.

Graphical abstract: Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids

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Article information

DOI
https://doi.org/10.1039/C1OB05113J
Article type
Communication
Submitted
21 Jan 2011
Accepted
08 Mar 2011
First published
08 Mar 2011

Org. Biomol. Chem., 2011,9, 3146-3150

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Stereoselective routes to aryl substituted γ-butyrolactones and their application towards the synthesis of highly oxidised furanocembranoids

A. P. G. Macabeo, A. Kreuzer and O. Reiser, Org. Biomol. Chem., 2011, 9, 3146 DOI: 10.1039/C1OB05113J

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