Total syntheses and biological investigations of tamandarins A and B and tamandarin A analogs.
Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.
Liang
B
B
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Richard
D J
DJ
Portonovo
P S
PS
Joullié
M M
MM
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D047630:Depsipeptides; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008958:Models, Molecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D014407:Tumor Cells, Cultured; D014561:Urochordata / Q000737:chemistry*
D000970:Antineoplastic Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C409142:tamandarin A; C433835:tamandarin B