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Communication | Regular issue | Vol 85, No. 2, 2012, pp.299-304
Published online, 10th January, 2012
DOI: 10.3987/COM-11-12397
Asymmetric Synthesis of (-)-Muricatacin’s Analogue (4S,5R)-5-Hydroxy-4-octadecanolide Exhibiting the Cytotoxicity against Esphageal Cancer Cells

Yow-Fu Tsai,* Chien-Cheng Huang, Shiau-Han Lin, Pei-Mei Su, Ying-Ju Chen, and Tzong-Yuan Wu

*Department of Chemistry, Chung Yuan Christian University, 200 Chung Pei Rd., Chung Li 23023, Taiwan, R.O.C.

Abstract

An efficient and facile synthesis, in six steps and 50% overall yield from commercial D-(-)-lyxose as starting material via twice Wittig olefination and one-pot deisopropylidenation and intramolecular lactonization, of the enantiopure (4S,5R)-(+)-5-hydroxy-4-octadecanolide (2), analogue of (-)-muricatacin, and the cytotoxic activity against CE48T cell line (human esophageal carcinoma) are described and the biological activity is the first shown in the literature.