Synthesis of unnatural amino acids from serine derivatives by beta-fragmentation of primary alkoxyl radicals.
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.
Boto
Alicia
A
Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206-La Laguna, Tenerife, Spain. alicia@ipna.csoc.es
Gallardo
Juan A
JA
Hernández
Dacil
D
Hernández
Rosendo
R
D000438:Alcohols / Q000737:chemistry; D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000438:Alcohols; D000596:Amino Acids; D005609:Free Radicals; C059688:alkoxyl radical; D012694:Serine