TY - JOUR
T1 - A versatile annulation protocol toward novel constrained phosphinic peptidomimetics
AU - Nasopoulou, Magdalini
AU - Georgiadis, Dimitris
AU - Matziari, Magdalini
AU - Dive, Vincent
AU - Yiotakis, Athanasios
PY - 2007/9/14
Y1 - 2007/9/14
N2 - (Chemical Equation Presented) The development of a novel 3-center 2-component annulation reaction between α,ω-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting α,ω-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochemistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.
AB - (Chemical Equation Presented) The development of a novel 3-center 2-component annulation reaction between α,ω-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting α,ω-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochemistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.
UR - http://www.scopus.com/inward/record.url?scp=34548781836&partnerID=8YFLogxK
U2 - 10.1021/jo071081l
DO - 10.1021/jo071081l
M3 - Article
C2 - 17715974
AN - SCOPUS:34548781836
SN - 0022-3263
VL - 72
SP - 7222
EP - 7228
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -