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.

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)