Allevi Pietro, Cribiù Riccardo, Giannini Elios, Anastasia Mario
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, via Saldini 50, I-20133 Milano, Italy.
J Org Chem. 2007 Apr 27;72(9):3478-83. doi: 10.1021/jo070136g. Epub 2007 Mar 31.
The paper reports some successful results on the first fully stereoselective total synthesis of the collagen cross-link pyridinolines. All stereogenic centers are stereoselectively introduced using Williams glycine template methodology, and oxazinones are used as a source of chirality and as easily removable protecting groups of the amino acidic functionalities during the assembly of the pyridinoline nucleus.