Synthesis of (R)-1-benzyloxy-3-buten-2-ol- a potential chiral synthon from L-(+)-tartaric acid: its applications in natural product syntheses

Rama Rao, A. V. ; Rajarathnam Reddy, E. ; Joshi, Bhalchandra V. ; Yadav, J. S. (1987) Synthesis of (R)-1-benzyloxy-3-buten-2-ol- a potential chiral synthon from L-(+)-tartaric acid: its applications in natural product syntheses Tetrahedron Letters, 28 (51). pp. 6497-6500. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4039(00)96898-9

Abstract

A practical synthesis of (R)-3-butene-1,2-diol derivatives from (R,R)-tartaric acid and their applications for the syntheses of (R)-ethyl-5-benzoyloxy-5-formyl pentanoate (2), a useful synthon for the preparation of arachidonic acid metabolites and (R)-γ-caprolactone (3), a pheromone of Trogoderma species, are described. A practical preparation of chiral building block 1 is described.

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