Abstract
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.
Publication types
-
Research Support, N.I.H., Extramural
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Amaryllidaceae Alkaloids / chemistry*
-
Amaryllidaceae Alkaloids / isolation & purification
-
Antineoplastic Agents, Phytogenic / chemical synthesis*
-
Antineoplastic Agents, Phytogenic / chemistry
-
Antineoplastic Agents, Phytogenic / pharmacology*
-
Drug Screening Assays, Antitumor
-
Humans
-
Molecular Structure
-
Narcissus / chemistry
-
Phenanthridines / chemistry*
-
Phenanthridines / isolation & purification
-
Plants, Medicinal / chemistry
-
Stereoisomerism
-
Structure-Activity Relationship
Substances
-
10b(s)-epipancratistatin
-
Amaryllidaceae Alkaloids
-
Antineoplastic Agents, Phytogenic
-
Phenanthridines
-
narciclasine