Synthesis of cryptophycin 52 using the Shi epoxidation.
[reaction: see text] A synthesis of cryptophycin 52 is reported using a Shi epoxidation strategy to install the epoxide moiety in a diastereoselective fashion. Several epoxidation results for cryptophycin substrates are disclosed followed by a discussion of the details relating to the preparation of cryptophycin 52 in two synthetic steps from one of the intermediate epoxides.
Hoard
David W
DW
Chemical Process Research and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, USA.
Moher
Eric D
ED
Martinelli
Michael J
MJ
Norman
Bryan H
BH
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides; D019008:Drug Resistance, Neoplasm; D004852:Epoxy Compounds / Q000138:chemical synthesis; D007769:Lactams / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D017239:Paclitaxel / Q000494:pharmacology
D000903:Antibiotics, Antineoplastic; D000972:Antineoplastic Agents, Phytogenic; D047630:Depsipeptides; D004852:Epoxy Compounds; D007769:Lactams; D007783:Lactones; C114033:cryptophycin 52; D017239:Paclitaxel