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J Org Chem. 2007 Sep 14;72(19):7260-9. Epub 2007 Aug 15.

Synthesis of unnatural amino acids from serine derivatives by beta-fragmentation of primary alkoxyl radicals.

Author information

1
Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206-La Laguna, Tenerife, Spain. alicia@ipna.csoc.es

Abstract

The fragmentation of primary alkoxyl radicals has been scarcely used in synthesis since other competing processes (such as oxidation or hydrogen abstraction) usually predominate. However, when serine derivatives were used as substrates, the scission took place in excellent yields. Tandem scission-allylation, -alkylation, or -arylation reactions were subsequently developed. This one-pot methodology was applied to the synthesis of unnatural amino acids, which are useful synthetic blocks or amino acid surrogates in peptidomimetics.

PMID:
17696478
DOI:
10.1021/jo071155t
[Indexed for MEDLINE]

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