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Org Lett. 2003 Mar 20;5(6):857-9. doi: 10.1021/ol0275264.

Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration.

Organic letters

Kanako Hirai, Hidenori Ooi, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama

Affiliations

  1. Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.

PMID: 12633090 DOI: 10.1021/ol0275264

Abstract

[reaction: see text] The first total synthesis of (+/-)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished based on Cr(II)/Ni(II)-mediated reaction of the aldehyde containing the citric acid moiety and the long-chain triflate, and the relative configuration of this natural product was determined.

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