The Total Synthesis of (−)-Callystatin A

✍ Scribed by Markus Kalesse; Khandavalli P. Chary; Monika Quitschalle; Arne Burzlaff; Cornelia Kasper; Thomas Scheper

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 190 KB
• Volume: 9
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200390130

✦ Synopsis

Callystatin A is a prominent member of a class of natural products which display promising growth inhibition of cancer cells in their biological profile. The challenging structure and the interesting biological activity of (-)-callystatin A fueled our interest in the synthesis of this marine natural product. We achieved the total synthesis using a highly convergent approach joining four subunits together with a Wittig olefination, a selective Heck reaction and an aldol reaction as the pivotal steps. The aldol reaction as one of the final transformations during the synthesis opens fast access to a variety of structural analogues and circumvents tedious protecting group manipulations. Here we report an improved synthesis utilizing a modified vinyl iodide which shortens the synthesis by two steps. Additionally, first biological results will be reported.