115215-55-9Relevant academic research and scientific papers
Stereoselective synthesis of hydroxy stilbenoids and styrenes by atom-efficient olefination with thiophthalides
Mitra, Prithiba,Shome, Brateen,Ranjan De, Saroj,Sarkar, Anindya,Mal, Dipakranjan
, p. 2742 - 2752 (2012/11/07)
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. The Royal Society of Chemistry 2012.
Synthesis of (+)-varitriol analogues via novel and versatile building blocks based on julia olefination
Senthilmnrugan, Annamalai,Aidhen, Indrapal Singh
experimental part, p. 555 - 564 (2010/04/24)
The synthesis of (+)-varitriol (1) analogues was achieved through, the use of Julia olefination. The potential anticancer properties of 1 coupled with, our interest in developing building blocks that enable olefin formation under the Julia protocol constitute the basis of our research project. Efforts are aimed at the synthesis of building blocks 2 and 3 and to explore their use towards the synthesis of (+)-varit:riol analogues. Herein, we would, like to present the synthesis of building block 3 and its ability to react with variety of substituted aromatic-, heterocyclic- and carbohydrate-derived aldehydes to yield alkene 6 in moderate to good yields with E as the major isomer. The successful, coupling of 2 with (furanoside moieties) aldehydes 5k, 5m and 5n in particular and the obtainment of compound 23 reflect the promise associated with the new strategy.
