Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451

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Partial Racemization Occurring in the Hydroxylactonization of a δ,ε-Epoxy Amide
Masaru ENOMOTO, Shigefumi KUWAHARA
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Keywords: dihydroisocoumarin, epoxy amide, hydroxylactonization, racemization, Baldwin rule
JOURNAL FREE ACCESS Advance online publication

Article ID: 100646

The final version of this article is now available: Vol. 74 (2010) , No. 12 p.2535
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Abstract

Acid-promoted hydroxylactonization of a δ,ε-epoxy amide took place via both 6-exo-tet and 7-endo-tet processes, causing a considerable degree of racemization of the resulting δ-hydroxyalkyl-δ-lactone.

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