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Synfacts 2009(6): 0589-0589  
DOI: 10.1055/s-0029-1216680
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 6-Deoxytetracycline

Contributor(s): Philip Kocienski
C. Sun, Q. Wang, J. D. Brubaker, P. M. Wright, C. D. Lerner, K. Noson, M. Charest, D. R. Siegel, Y.-M. Wang, A. G. Myers*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

A short, efficient synthesis of 6-deoxytetracycline entails a Michael-Claisen condensation of the AB-ring precursor C and the D-ring precursor A. A library of over 50 tetracycline analogues was prepared by similar condensations of a wide range of D-ring precursors (e.g., A where R = aryl or hetaryl) with C or C′. Quinoline, pyridine and naphthalene D-ring analogues of A were also used.