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

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.

SUBMITTER: Pettit GR

PROVIDER: S-EPMC2782413 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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

Pettit George R GR Melody Noeleen N Thornhill Andrew A Knight John C JC Groy Thomas L TL Herald Cherry L CL

Journal of natural products 20090901 9

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) ...[more]

PMID: 19719153

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