Enantioselective synthesis of (+)-chamaecypanone C: a novel microtubule inhibitor.
A bicycle built for tubulin: The total synthesis of (+)-chamaecypanone C has been achieved by using a tandem retro-Diels-Alder/Diels-Alder cascade reaction (see scheme). Initial biological studies demonstrate that (+)-chamaecypanone C is an inhibitor of tubulin assembly and binds at the colchicine site.
Dong
Suwei
S
Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA.
Hamel
Ernest
E
Bai
Ruoli
R
Covell
David G
DG
Beutler
John A
JA
Porco
John A
JA
D000818:Animals; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D048328:Potoroidae; D051381:Rats; D013237:Stereoisomerism; D050257:Tubulin Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D001643:Bridged Bicyclo Compounds; D050257:Tubulin Modulators; C539295:chamaecypanone C