Synthesis of (+)-decarestrictine L

✍ Scribed by Julie M. Lukesh; William A. Donaldson

• Book ID: 104359729
• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 251 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00126-5

✦ Synopsis

A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl-D-glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield.