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College of Chemistry

2003 News Index

Trauner Group Synthesizes Mollusk Molecule

From Chemical & Engineering News, Science Concentrates, Feb. 10, 2003

Chemists have accomplished the total synthesis of photodeoxytridachione, one of a range of interesting biologically active compounds produced by shell-less sacoglossan mollusks [Angew. Chem. Int. Ed., 42, 549 (2003)]. Chemistry assistant professor Dirk Trauner and graduate student Aubry K. Miller say their synthetic strategy involves creating a precursor common to many of these compounds, which should make additional syntheses possible. The mollusks, which use algae chloroplasts to carry out photosynthesis in their own tissues, produce two classes of these defensive natural products: bicyclohexenes, of which photodeoxytridachione is a member, and cyclohexadiene derivatives. Trauner and Miller devised a new general reaction, using a Lewis acid to catalyze the cyclization of hexatrienes to bicyclo[3.1.0]hexenes. This reaction, in turn, allowed them to synthesize photodeoxytridachione. They are now working to synthesize other molluskan polypropionates.

Related sites:

Dirk Trauner research page

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