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ChemInform Abstract: A Novel Three-Step Hydroxy-Deamination Sequence: Conversion of Lysine to 6-Hydroxynorleucine Derivatives.

✍ Scribed by C. R. JUN. NEVILL; P. T. ANGELL

Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

A Novel Three-Step Hydroxy-Deamination Sequence: Conversion of Lysine to 6-Hydroxynorleucine Derivatives.

-L-lysine (I) is converted into a series of totally protected derivatives such as (IV), which are oxidized with catalytic RuO 4 to give the corresponding acyl carbamates, e.g. (V). Selective reduction of the acyl carbamate is achieved only in the presence of a t-butyl ester, yielding the desired 6-hydroxynorleucine ester (VI). By contrast, methyl and ethyl ester analogues of (V) undergo competitive reduction of the ester moiety.

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