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Synthesis 2009(14): 2418-2422  
DOI: 10.1055/s-0029-1216855
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Concise Total Synthesis of (+)-Disparlure and its trans-Isomer Using Asymmetric Organocatalysis

Sung-Gon Kim*
Department of Chemistry, College of Natural Science, Kyonggi University, San 94-6, Iui-dong, Yeongtong-gu, Suwon 443-760, Korea
Fax: +82(31)2499631; e-Mail: sgkim123@kgu.ac.kr;
Further Information

Publication History

Received 25 February 2009
Publication Date:
29 May 2009 (online)

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Abstract

The efficient enantioselective synthesis of (+)-disparlure and its trans-isomer is described. This approach involves tandem asymmetric organocatalytic α-aminoxylation-allylation of an aldehyde and olefin cross metathesis using Grubbs’ catalyst as key steps.

Key words

disparlure - total synthesis - organocatalysis - asymmetric synthesis - olefin cross metathesis

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11

The ratio of E/Z-regioisomers in 10 (1:5), which was estimated by ¹³C NMR spectroscopy, was not important because the double bond was reduced by hydrogenation in the next step.

13

We have found that Grubbs’ catalyst cleanly cleaved the N-O bond of 4 to furnish diol in the case of the absence of a cross-metathesis partner; detailed results will be published in due course.