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Review | Regular issue | Vol 36, No. 2, 1993, pp.359-388
Published online, 1st January, 1970
DOI: 10.3987/REV-92-453
The Detoxin Complex. — A Naturally Occurring Safener

Wen-Ren Li, So-Yeop Han, and Madeleine M. Joullié*

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.

Abstract

The detoxin complex is a group of depsipeptide metabolites produced by the organism Streptomyces caespitosus var. detoxicus 7072GC1 as well as other strains of streptomyces. The complex is the first isolated natural product which displays a unique detoxification effect in plant and animal cells as its biological actvity. The structural investigations carried out to elucidate the structures of the congeners and the stereochemistry of the stereogenic centers are described. Structure-activity relationships are discussed. The different synthetic approaches to the parent amino acid, (-)-detoxinine, are compared. The syntheses of detoxins (-)-B1, (-)-B3, (-)-D1, and (+)-valyldetoxinine are described.