Total synthesis of ipomoeassin F.
The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathesis was used to form the macrocyclic ring, and seven more steps then furnished ipomoeassin F. In vitro inhibitory activity against a four-panel cell line showed low nanomolar inhibitory activity.
Postema
Maarten H D
MH
Department of Discovery Chemistry, Eisai Research Institute, 4 Corporate Drive, Andover, Massachusetts 01810, USA. maarten_postema@eri.eisai.com
TenDyke
Karen
K
Cutter
James
J
Kuznetsov
Galina
G
Xu
Qunli
Q
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006031:Glycosylation; D006801:Humans; D027741:Ipomoea / Q000737:chemistry; D015394:Molecular Structure
D000972:Antineoplastic Agents, Phytogenic; D001688:Biological Products; D006001:Glycoconjugates; C523857:ipomoeassin F