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DOI: 10.1055/s-2004-825582
Preparation of an Advanced Phenylglycine-Derived Intermediate en route to the Southern Hemisphere Tetraene of Viridenomycin
Publication History
Publication Date:
10 May 2004 (online)
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Abstract
A high-yielding synthesis of a phenylglycine derived (E,Z)-dienylboronate en route to the C16-C23 tetraene of the polyene macrolide viridenomycin is described. Crucial to this synthesis was the development of conditions enabling ready access to synthetically useful amino acid derivatives that should be widely applicable to other amino acids. These conditions confer advantages of increased yield and reliability over many of the existing literature alternatives, and also circumvent several of the problems encountered when dealing with such derivatives. The synthesis features a highly selective Heck coupling between an N-protected (Z)-alkenyl iodide and a hexylene glycol derived vinylboronate ester.
Key words
natural product - palladium - Heck reaction - asymmetric synthesis - amino alcohol
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