Abstract
As an extension of our earlier structure/activity investigation of resveratrol (1a) cancer cell growth inhibitory activity compared to the structurally related stilbene combretastatin series (e.g., 2a), an efficient synthesis of E-stilstatin 3 (3a) and its phosphate prodrug 3b was completed. The trans-stilbene 3a was obtained using a convergent synthesis employing a Wittig reaction with phosphonium bromide 9 as the key reaction step. Deprotection of the Z-silyl ether 13 gave E-stilstatin 3 (3a) as the exclusive product. The structure and stereochemistry of 3a was confirmed by X-ray crystal structure determination.
Original language | English (US) |
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Pages (from-to) | 1637-1642 |
Number of pages | 6 |
Journal | Journal of Natural Products |
Volume | 72 |
Issue number | 9 |
DOIs | |
State | Published - Sep 25 2009 |
ASJC Scopus subject areas
- Analytical Chemistry
- Molecular Medicine
- Pharmacology
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry
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CCDC 736738: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Melody, N. (Creator), Thornhill, A. (Creator), Knight, J. C. (Creator), Groy, T. L. (Creator), Herald, C. L. (Creator) & Pettit, G. R. (Creator), The Cambridge Structural Database, 2016
DOI: 10.5517/ccdc.csd.ccsqmrv, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.ccsqmrv&sid=DataCite
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