TOTAL SYNTHESIS OF (-)-THIANGAZOLE AND STRUCTURALLY RELATED POLYAZOLES

被引：58

作者：

WIPF, P

VENKATRAMAN, S

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 22期

关键词：

D O I：

10.1021/jo00127a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thiangazole was reported to be an extremely potent, nontoxic inhibitor of HIV-1 in MT4 cell assays. By employing a strategy of selective oxazoline-thiazoline interconversions, we have accomplished a total synthesis of the natural product in 16 steps and 1.1% overall yield from (S)-alpha-methylserine. This new methodology is especially useful for the preparation of analogs of thiangazole and structure-activity studies. Our preliminary biological testing of (-)-thiangazole revealed a high level of cytotoxicity that was considerably reduced in the oxazoline-containing analogs.

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页码：7224 / 7229

页数：6

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