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.

Details

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 )