Issue 19, 2003
From the journal:

Organic & Biomolecular Chemistry

Synthesis of (−)-Gloeosporone, a fungal autoinhibitor of spore germination using a π-allyltricarbonyliron lactone complex as a templating architecture for 1,7-diol construction†

Steven V. Ley,*a   Ed Cleator,a   Jürgen Hartera  and  Christopher J. Hollowooda  

* Corresponding authors

a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk
Fax: +44 (0) 1223 336442
Tel: +44 (0) 1223 336398

Abstract

The synthesis of the germination self-inhibitor (−)-Gloeosporone is reported. The embedded 1,7-diol motif in the product is constructed by an ironcarbonyl tether controlled Mukaiyama aldol reaction. The key step in the synthesis is the reductive removal of the ligating iron species by treatment of an acetoxycomplex 6 with lithium naphthalenide.

Graphical abstract: Synthesis of (−)-Gloeosporone, a fungal autoinhibitor of spore germination using a π-allyltricarbonyliron lactone complex as a templating architecture for 1,7-diol construction

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Article information

DOI
https://doi.org/10.1039/B308793J
Article type
Communication
Submitted
28 Jul 2003
Accepted
20 Aug 2003
First published
29 Aug 2003

Org. Biomol. Chem., 2003,1, 3263-3264

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Synthesis of (−)-Gloeosporone, a fungal autoinhibitor of spore germination using a π-allyltricarbonyliron lactone complex as a templating architecture for 1,7-diol construction

S. V. Ley, E. Cleator, J. Harter and C. J. Hollowood, Org. Biomol. Chem., 2003, 1, 3263 DOI: 10.1039/B308793J

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