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ABSTRACT: A stereoselective synthesis of the hydroxyethylene dipeptide isostere 1 is described. The route employs a substrate-directed kinetic protonation of an alpha/gamma-substituted lactone to afford the desired stereochemistry. A method for converting the diastereomerically enriched intermediate lactone to the ring-open form with retention of stereochemistry is demonstrated. A novel procedure for utilizing N,N-dibromo-5,5-dimethylhydantoin in Hofmann rearrangements is disclosed. This route was used to prepare amino alcohol 1, the core portion of the HIV protease inhibitor A-792611, in 46% yield from phenylalanine-derived epoxide 2.
The Journal of Organic Chemistry 08/2006; 71(14):5369-72. · 4.45 Impact Factor
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Eric J Stoner,
Michael S Allen,
Alan C Christesen,
Rodger F Henry, L Steven Hollis,
Robert Keyes,
Ian Marsden,
Tamara C Rehm,
Sandeep G Shiroor,
Niru B Soni,
Kent D Stewart
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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.
The Journal of Organic Chemistry 05/2005; 70(8):3332-5. · 4.45 Impact Factor
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Tetrahedron. 60(47):10611-10618.
