Stereoselective total synthesis of (±)-isolobophytolide, a marine cembranolide natural product

✍ Scribed by James A. Marshall; Robert C. Andrews

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 277 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85167-9

✦ Synopsis

The total synthesis of ( Z!I l-isolobophytolide (20) has been achieved via a route involving piallvl oalladium initiated macrocvclization of sulfone ester 8 and subseauent carboxv inversion of the ma"cr&yclic acid 11 to introduce-the C-14 lactone oxygen. Lactone a-rnethylenatiok was effected by dehydration of the hydroxymethyl derivative I9 with 1-cyclohexyl-3-(2-morpholinoethyllcarbodiimide metho-p-toluenesulfonate-CuClz.