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Synthesis of (+)‐Varitriol Analogues via Novel and Versatile Building Blocks Based on Julia Olefination
Author(s) -
Senthilmurugan Annamalai,
Aidhen Indrapal Singh
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901012
Subject(s) - chemistry , yield (engineering) , combinatorial chemistry , olefin fiber , block (permutation group theory) , alkene , organic chemistry , catalysis , materials science , geometry , mathematics , metallurgy
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 (+)‐varitriol 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.