Synthesis of (+)-methyl (R,E)-6-benzyloxy-4-hydroxy-2-hexenoate and its mesylate derivative

Article abstract of DOI:10.1080/00397919508011364

Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield.

Full text of DOI:10.1080/00397919508011364

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Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
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Synthesis of (+)-Methyl (R,E)-6-
Benzyloxy-4-hydroxy-2-
hexenoate and Its Mesylate
Derivative
P. de March a , M. Figueredo a , J. Font a & M.
Monsalvatje a
a Unitat de Química Orgánica , Universitat Autònoma
de Barcelona , 08193, Bellaterra, Spain
Published online: 23 Sep 2006.
To cite this article: P. de March , M. Figueredo , J. Font & M. Monsalvatje
(1995) Synthesis of (+)-Methyl (R,E)-6-Benzyloxy-4-hydroxy-2-hexenoate and
Its Mesylate Derivative, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 25:3, 331-342, DOI:
10.1080/00397919508011364
To link to this article: http://dx.doi.org/10.1080/00397919508011364
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