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Synthesis 2004(9): 1343-1348  
DOI: 10.1055/s-2004-822388
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Acetomycin Bislactone Analogues

Jun’ichi Uenishi*, Hironobu Muraoka, Masatake Nameki, Naoko Hata
Kyoto Pharmaceutical University, Misasagi-Shichounocho, Yamashina, Kyoto 607-8412, Japan
Fax: +81(75)5954763; e-Mail: juenishi@mb.kyoto-phu.ac.jp;
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Publikationsverlauf

Received 15 April 2004
Publikationsdatum:
26. Mai 2004 (online)

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Abstract

Bislactones 5 and 6 have been designed as esterase-resistant acetomycin analogues and prepared in 10 steps from methyl 2-methylacetoacetate. Consecutive quaternary and tertiary carbon centers at the C-3 and C-4 positions on the γ-lactone ring are constructed by Pd-catalyzed allylic alkylation in one step. The relative stereochemistry for 6 has been determined by X-ray crystallographic analysis.

Key word

bioorganic chemistry - palladium - esterase - stereoselective synthesis - γ-lactone

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