The Total Synthesis of (-)-Callystatin A

verfasst von

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.

Organisationseinheit(en)

Institut für Organische Chemie
Institut für Technische Chemie

Typ

Artikel

Journal

Chemistry - a European journal

Band

9

Seiten

1129-1136

Anzahl der Seiten

8

ISSN

0947-6539

Publikationsdatum

21.02.2003

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Katalyse, Organische Chemie

Ziele für nachhaltige Entwicklung

SDG 3 – Gute Gesundheit und Wohlergehen, SDG 14 – Lebensraum Wasser

Elektronische Version(en)

https://doi.org/10.1002/chem.200390130 (Zugang: Unbekannt)