ChemInform Abstract: Total Synthesis and Absolute Configuration of Polycavernoside A.

✍ Scribed by K. FUJIWARA; A. MURAI; M. YOTSU-YAMASHITA; T. YASUMOTO

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 38 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199910213

✦ Synopsis

Total Synthesis and Absolute Configuration of Polycavernoside A.

-The first total synthesis of polycavernoside A (XII), a toxin of red alga species, is presented, involving formation of the cyclic acetal (IV), lactonization of secoic acid (V) and rearrangement of the obtained 12-membered lactone (VII) to 13-membered cyclic hemiacetal (VIII). Glycosidation and cross-coupling of the so formed glycoside (X) with dienyl mercury (XI) affords the title compound (XII) which is characterized by means of CD spectra. -(FUJIWARA, K.;