Synthetic studies towards the squalestatins and zaragozic acids

✍ Scribed by Leasa M. McVinish; Mark A. Rizzacasa

• Book ID: 104215686
• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 293 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)76001-1

✦ Synopsis

A synthesis of a mod core sysmn (18) of the sqdestatins and saragozic acids has been achieved y?om D-mannose. The key steps intive an Irehd-Chisen reawan~emeni of the ally1 ester 5 ad a stereoselective epoxidktion of the f&add glycd 12 with 2&dimethyl&xkne. A number of structurally related compounds have been isolated by two independent groups in screening pmgrams for inhibitors of squalene synthase, the enzyme which catalyses the firs pathway-specific step in stem1 biosynthesis. These agents were named the squalestatins-1 (0, -2 (2) and -3 (3) (isolated from the fungus Phma sp. C2932)l and the zaragozic acids A (1). B and C (isolated from the two fkngal cultures Sporormiella intermedia and Lcprodonitium elatius). 2 The structures were assigned by a combination of