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Synlett 2008(4): 513-516
DOI: 10.1055/s-2008-1042756
DOI: 10.1055/s-2008-1042756
LETTER
© Georg Thieme Verlag Stuttgart · New York
Chemoenzymatic and Chemical Routes to the Nonproteinaceous Amino Acid Albizziine and Its Amide Derivative
Further Information
Received
14 November 2007
Publication Date:
12 February 2008 (online)
Publication History
Publication Date:
12 February 2008 (online)
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Abstract
A two-step route for the synthesis of albizziine from Nα-Boc-asparagine which proceeds in 65% overall yield is disclosed. A high-yielding, six-step route for the synthesis of its protected amido derivative gives rapid access to a key component of the complex aminopolyol natural product, zwittermicin A.
Key words
d-amino acid oxidase - Hoffmann rearrangement - amidation - urea formation
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References and Notes
Boc deprotection using TFA, TFA-CH2Cl2, or HCl-dioxane, was found to be unsuccessful in this instance.