6533b86dfe1ef96bd12c9e01

RESEARCH PRODUCT

The Synthesis of Bioactive Sesquiterpenes from Santonin

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Abstract This article reviews the literature published in the last decade dealing with the transformation of α-santonin into bioactive or potentially bioactive sesquiterpenes. A number of syntheses starting from 8α-hydroxysantonin (artemisin) have also been included. Special emphasis has been placed on synthesized products that show biological activity. Major advances in this field include the application of new reagents and methodologies for the structural modification of the santonin skeleton and functionality, and its transformation into other sesquiterpenes, especially sesquiterpene lactones. The review has been organised into five parts: 1. Introduction: An overview of the structure and biological activity of the starting material santonin. 2. Synthesis of 6,12-sesquiterpenolides: This section describes the synthesis of sesquiterpenes bearing a lactone moiety between C(6) and C(12). The transformation of the A-ring in santonin to give eudesmanolides, guaianolides, and elemanolides, as well as the modification of the lactone ring is described. Some microbiological transformations of santonin and its derivatives are also described. 3. Synthesis of 8,12-sesquiterpenolides: This section describes the oxy-functionalization of C(8) in santonin and its transformation into other sesquiterpenes with a lactone moiety between C(8) and C(12). 4. Synthesis of sesquiterpenes that do not contain a lactone moiety. 5. Miscellaneous: In this section, a number of structural modifications of santonin that do not lead to natural products, but that may be of synthetic interest, are described.