Organic & Biomolecular Chemistry 2012-04-14

Stereoselective synthesis of hydroxy stilbenoids and styrenes by atom-efficient olefination with thiophthalides.

Prithiba Mitra, Brateen Shome, Saroj Ranjan De, Anindya Sarkar, Dipakranjan Mal

Index: Org. Biomol. Chem. 10(14) , 2742-52, (2012)

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Abstract

The synthesis of stilbenoids and styryl carboxylic acids is accomplished with high E-stereoselectivity by olefination of aldehydes with thiophthalides under basic conditions. The olefination is highly atom-efficient as it only loses elemental sulfur during the reaction. This olefination, in conjunction with retro Kolbe-Schmitt reaction, allows facile synthesis of E-hydroxystilbenoids with minimal employment of protecting groups. This study also discloses two important findings: formation of i) 4-methylsulfanyl isocoumarins and ii) an 2-arylindenone.This journal is © The Royal Society of Chemistry 2012