Synthetic studies of tedanolide, a marine macrolide displaying potent antitumor activity. Stereoselective synthesis of the C13-C23 segment.
[structure: see text] A highly stereoselective synthesis of the C13-C23 segment of tedanolide (1), an 18-membered macrolide isolated from the Caribbean sponge Tedania ignis, displaying significant cytotoxicity against KB and PS tumor cell lines, is described which involves two stereoselective epoxidations of regioisomeric trisubstituted double bonds and a stereospecific S(N)2' methylation reaction of a trans-gamma,delta-epoxy-cis-alpha,beta-unsaturated ester as the key steps.
Iwata
Yasuhiro
Y
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
Tanino
Keiji
K
Miyashita
Masaaki
M
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis / Q000494:pharmacology; D018942:Macrolides / Q000138:chemical synthesis* / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D007783:Lactones; D018942:Macrolides; C119775:tedanolide