Stereoselective Synthesis of (+)-Eldanolide Using a Chiral Sulfoxide

Chem. J. Chinese Universities ›› 1995, Vol. 16 ›› Issue (9): 1391.

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Stereoselective Synthesis of (+)-Eldanolide Using a Chiral Sulfoxide

XU Zhang-Huang¹, HUANG Jin-Xia¹, LI Yan¹, CHEN Zu-Xing¹, GAO Ming-Zhang²

1. Department of Chemistry Hubei University, Wuhan, 430062;
2. Department of Chemistry, Xijiang University, Zhaoqing

Received:1994-09-21 Revised:1995-02-20 Online:1995-09-24 Published:1995-09-24

Abstract

Abstract: In this paper,(+)-Eldanolide,one of the pheromones of the male African sugarcane borer (Eldana Saccharina), was stereoseiectively synthesized by employing Michael addition of (+)-(R )-4-methyl-1-(p-tolysulfinyl)-3-pentene to trans-methyl crotonate, deoxygenation of the sulfoxide group by sodium iodide and trifluoroacetic anhydride,regioselective methylation by trimethyloxonium tetrafluoroborate and stereospecific lactonation by potassium t-butoxide through an S_N2 mechanism. The enantiomeric excess of the total synthesis is about 39% e.e.and the ratio of trans-and cis-disubstituted lactones is trans: cis= 92: 8.

Key words: Eldanolide, Chiral sulfoxide, Michael addition

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XU Zhang-Huang, HUANG Jin-Xia, LI Yan, CHEN Zu-Xing, GAO Ming-Zhang. Stereoselective Synthesis of (+)-Eldanolide Using a Chiral Sulfoxide[J]. Chem. J. Chinese Universities, 1995, 16(9): 1391.

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Stereoselective Synthesis of (+)-Eldanolide Using a Chiral Sulfoxide

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