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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 417-422 |
| Number of pages | 6 |
| Journal | Journal of Natural Products |
| Volume | 70 |
| Issue number | 3 |
| DOIs | |
| State | Published - Mar 2007 |
ASJC Scopus subject areas
- Analytical Chemistry
- Molecular Medicine
- Pharmacology
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry
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CCDC 643567: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Melody, N. (Creator), Herald, D. L. (Creator), Knight, J. C. (Creator), Chapuis, J. (Creator) & Pettit, G. R. (Creator), The Cambridge Structural Database, 2007
DOI: 10.5517/ccplp75, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccplp75&sid=DataCite
Dataset
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CCDC 643566: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Melody, N. (Creator), Herald, D. L. (Creator), Knight, J. C. (Creator), Chapuis, J. (Creator) & Pettit, G. R. (Creator), The Cambridge Structural Database, 2007
DOI: 10.5517/ccplp64, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccplp64&sid=DataCite
Dataset