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Synthesis 2001(12): 1790-1793
DOI: 10.1055/s-2001-17514
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Triketide δ-Lactones

Sang-Jung Kima, Han-Young Kang*a, David H. Shermanb
a Department of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Korea
b Department of Microbiology and Biological Process Technology Institute, University of Minnesota, Minneapolis, Minnesota 55455, USA
Fax: +82(43)2672279; e-Mail: hykang@chungbuk.ac.kr;
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Publication History

Received 23 March 2001
Publication Date:
11 August 2004 (online)

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Abstract

An efficient synthetic route was developed to prepare substituted δ-lactones 1 and 2 in enantiopure forms which are potentially useful for biosynthetic studies with genetically engineered modular polyketide synthase (PKS). The key step to prepare the target epimeric lactones involves the samarium(II) iodide-mediated Reformatsky reaction.

Key words

polyketide biosynthesis - lactones - samarium(II) iodide - aldol reaction - Reformatsky reaction