Preparation of an advanced phenylglycine-derived intermediate en route to the southern hemisphere tetraene of viridenomycin

Maw, G.N.; Thirsk, C.; Toujas, J.L.; Vaultier, M.; Whiting, A.

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.

Citation

Maw, G., Thirsk, C., Toujas, J., Vaultier, M., & Whiting, A. (2004). Preparation of an advanced phenylglycine-derived intermediate en route to the southern hemisphere tetraene of viridenomycin. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 1183-1186

• Journal Article Type: Article
• Publication Date: 2004-06
• Journal: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
• Print ISSN: 0936-5214
• Publisher: Thieme Gruppe
• Peer Reviewed: Peer Reviewed
• Issue: 7
• Pages: 1183-1186