935853-68-2Relevant academic research and scientific papers
Antineoplastic agents. 550. Synthesis of 10b(S)-epipancratistatin from (+)-narciclasine
Pettit, George R.,Melody, Noeleen,Herald, Delbert L.,Knight, John C.,Chapuis, Jean-Charles
, p. 417 - 422 (2008/02/04)
By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.
