Total synthesis of (+)-varitriol via a symmetrical furanose diol as the key intermediate

• Published in: Tetrahedron letters Vol. 52; no. 52; pp. 7075 - 7078
• Main Authors: Nagarapu, Lingaiah, Paparaju, Venkateswarlu, Satyender, Apuri, Bantu, Rajashaker
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 28.12.2011; Elsevier
• Subjects: (+)-Varitriol; Alcohols; Analogues; Anti-cancer activity; Antineoplastic agents; Biological; Biological and medical sciences; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Diols; Exact sciences and technology; General aspects; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Medical sciences; Natural products; Noncondensed benzenic compounds; Organic chemistry; Pharmacology. Drug treatments; Physical Sciences; Preparations and properties; Science & Technology; Strategy; Symmetrical diol; Synthesis (chemistry); Tetrahedrons; Total synthesis; Symmetrical diol; (+)-Varitriol; Analogues; Total synthesis; Anti-cancer activity; EFFICIENT TOTAL-SYNTHESIS; ACID; CHIRAL TRANSFORMATIONS; ANALOGS; D-RIBOSE; VARITRIOL; DERIVATIVES; Antineoplastic agent; Diol; Aldose; Furan derivatives; Alcohol; Oside; Natural compound; Oxygen heterocycle; Biological activity; Furanose; Marine environment; Structure activity relation; Ribose; Styrene derivatives; Chemical synthesis; Protection
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.10.076

Synthesis of (+)-varitriol has been achieved from d-ribose via a symmetrical furanoside diol as the key intermediate, which is also a very useful furanoside building block in synthesizing novel analogues of (+)-varitriol. Alternative, simple and efficient route for (+)-varitriol (1), a marine-derived natural product with potent biological activity, has been synthesized from d-ribose. In this synthetic strategy symmetrical diol (6) with mono alcohol protection, the key intermediate, was produced in eight steps with 35% overall yield and the significance of 6 as the key furanoside building block for the synthesis of novel analogues of 1 for SAR studies was explained.