Transformation of Vitamin B6 to (+)-Deoxypyridinoline, a useful Biochemical Marker for Diagnosis of Bone Diseases

A versatile chiral synthesis of the cross-link (+)-deoxypyridinoline (Dpd, 2) was achieved starting from vitamin B6 (7). The key steps in the synthesis of (+)-2 are transformation of B6 (7) to the chloride (3d) and construction of three α-amino acid chains by utilizing (R)-(−)-Schollkopfʹs reagent (4), Wittig reagent (R)-(−)-5, and iodide (S)-(−)-6. (+)-Dpd (2) is a degradation product of bone collagen and has been found to be a useful marker for diagnosis of osteoporosis and other metabolic bone diseases.