The Total Synthesis of (-)-Callystatin A

Authored by

Markus Kalesse, Khandavalli P. Chary, Monika Quitschalle, Arne Burzlaff, Cornelia Kasper, Thomas Scheper

Abstract

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.

Details

Organisation(s): Institute of Organic Chemistry
Institute of Technical Chemistry
Type: Article
Journal: Chemistry - a European journal
Volume: 9
Pages: 1129-1136
No. of pages: 8
ISSN: 0947-6539
Publication date: 21.02.2003
Publication status: Published
Peer reviewed: Yes
ASJC Scopus subject areas: Catalysis, Organic Chemistry
Sustainable Development Goals: SDG 3 - Good Health and Well-being, SDG 14 - Life Below Water
Electronic version(s): https://doi.org/10.1002/chem.200390130 (Access: Unknown )