Total synthesis of (+/-)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi.
The title alkaloid 1 and its B-nor-congener 3, both of which display potent and unusual anti-mitotic properties, have been synthesized in racemic form and characterised by single-crystal X-ray analysis.
Banwell
Martin G
MG
Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au
Edwards
Alison J
AJ
Jolliffe
Katrina A
KA
Smith
Jason A
JA
Hamel
Ernest
E
Verdier-Pinard
Pascal
P
D000447:Aldehydes / Q000138:chemical synthesis* / Q000494:pharmacology*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D016195:G2 Phase / Q000187:drug effects; D006801:Humans; D007212:Indolizines / Q000138:chemical synthesis* / Q000494:pharmacology*; D008958:Models, Molecular; D017239:Paclitaxel / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014404:Tubulin / Q000737:chemistry / Q000187:drug effects; D014747:Vinblastine / Q000494:pharmacology
D000447:Aldehydes; D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D007212:Indolizines; D014404:Tubulin; C480458:rhazinal; D014747:Vinblastine; D017239:Paclitaxel