Pharmaco-chemistry of Malaysian timber trees - IX synthesis of resveratrol analogues and potential gamma-butyrolactone precursors of biologically active oligostilbenoids

Thomas N.F., . and Thomas Paraidathathu, . and Weber J.F.F, . and Rashwan H., . and Lee K.C., . and Velu S.S., . and Tay I.I., . and Juraimi H., . and Abdul Hadi A.H., . and Awang K., . and Shari K., . (2001) Pharmaco-chemistry of Malaysian timber trees - IX synthesis of resveratrol analogues and potential gamma-butyrolactone precursors of biologically active oligostilbenoids. [Proceedings Paper]

Functionalised gamma-butyrolactones have been identified as precursors of the pharmacologically active oligostilbenoid dimer epsilon-viniferin. Ina related investigation the palladium catalysed coupling of benzylprotected iodophenol and 3 5-dimethoxystyrene the Heck Reaction has produced a novel resveratrol analgue in moderate to good yield in our first attempt. We hope to synthesize resveratrol and other potent stilbenoids by this procedure. The precursors for our Heck reaction have been successfully prepared by conventional benzylation and Wittig reaction methodologies. This particular application of Heck reaction chemistry may well be unprecedented. Attempted oxidative lactonisation of some our novel stilbenes with manganese triacetate gave some unexpected results.

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Abstract

Functionalised gamma-butyrolactones have been identified as precursors of the pharmacologically active oligostilbenoid dimer epsilon-viniferin. Ina related investigation the palladium catalysed coupling of benzylprotected iodophenol and 3 5-dimethoxystyrene the Heck Reaction has produced a novel resveratrol analgue in moderate to good yield in our first attempt. We hope to synthesize resveratrol and other potent stilbenoids by this procedure. The precursors for our Heck reaction have been successfully prepared by conventional benzylation and Wittig reaction methodologies. This particular application of Heck reaction chemistry may well be unprecedented. Attempted oxidative lactonisation of some our novel stilbenes with manganese triacetate gave some unexpected results.

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Item Type:	Proceedings Paper
Additional Information:	Perpustakaan Sultan Abdul Samad Universiti Putra Malaysia 43400 UPM Serdang Selangor Malaysia. QD415 A1N277 2000
AGROVOC Term:	TIMBER TREES
AGROVOC Term:	PHARMACOLOGY
AGROVOC Term:	PHENOLIC COMPOUNDS
AGROVOC Term:	DRUG PLANTS
AGROVOC Term:	AROMATIC COMPOUNDS
AGROVOC Term:	MALAYSIA
Geographical Term:	MALAYSIA
Depositing User:	Ms. Norfaezah Khomsan
Last Modified:	24 Apr 2025 05:27
URI:	http://webagris.upm.edu.my/id/eprint/15950

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