Antineoplastic agents. 579. Synthesis and cancer cell growth evaluation of E-stilstatin 3: a resveratrol structural modification

J Nat Prod. 2009 Sep;72(9):1637-42. doi: 10.1021/np9002146.

George R Pettit ¹, Noeleen Melody, Andrew Thornhill, John C Knight, Thomas L Groy, Cherry L Herald

Affiliations

Affiliation

1 Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287-1604, USA. bpettit@asu.edu

PMID: 19719153 DOI: 10.1021/np9002146

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.

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