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An unusual intramolecular hetero-Diels-Alder cycloaddition.

Stoner, Eric J; Allen, Michael S; Christesen, Alan C; Henry, Rodger F; Hollis, L Steven; Keyes, Robert; Marsden, Ian; Rehm, Tamara C; Shiroor, Sandeep G; Soni, Niru B; Stewart, Kent D.

J Org Chem ; 70(8): 3332-5, 2005 Apr 15.

Article in English | MEDLINE | ID: mdl-15823010

ABSTRACT

A new reaction of erythronolides, an intramolecular hetero-Diels-Alder, has been discovered. Heated aqueous alcoholic solutions of ABT-773 (1) and its cis isomer (3) convert slowly to cycloadducts 2 and 4, respectively. Optimal reaction conditions, mechanistic studies supported by molecular modeling, and biological activity data are reported. Single-crystal X-ray structures for both adducts 2 and 4 have been obtained.

Subject(s)

Erythromycin/analogs & derivatives , Erythromycin/chemistry , Ketolides/chemistry , Catalysis , Crystallography, X-Ray , Cyclization , Molecular Conformation , Molecular Structure , Stereoisomerism

ABSTRACT

Subject(s)

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