Synthesis of (+)-Varitriol Analogues via Novel and Versatile Building Blocks Based on Julia Olefination

✍ Scribed by Annamalai Senthilmurugan; Indrapal Singh Aidhen

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 537 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200901012

✦ Synopsis

Abstract

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.