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

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-derive...

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Veröffentlicht in:Tetrahedron letters 2011-12, Vol.52 (52), p.7075-7078
Hauptverfasser: Nagarapu, Lingaiah, Paparaju, Venkateswarlu, Satyender, Apuri, Bantu, Rajashaker
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Sprache:eng
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Zusammenfassung: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.10.076