An approach to 2,3-methanoamino acids with extended side chanis: syntheses of trans-BOC-cyclo-lys(CBZ)-OH, trans-BOC-cyclo-Glu-Oet, and trans-BOC-cyclo-Arg(CBZ)-Oh

摘要

lactone 1, available as either antipode from D-amannitol or L-gulono-1,4-lactone, is a valuable starting material for syntheses of methanoamino acids with 3-substituents that are functionalized methylene groups (CH_2X, X= heteroatom). For instance, it has been used to prepare the 2,3-methanoamino acids 2 and 3 efficiently. Chiron 1 also has been used in syntheses of 2,3-methanoamino acids with functionalized ethylene substituents (CH_2- CH_2X, X= heteroatom).