Transformation of vitamin B-6 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 B-6 (7). The key steps in the synthesi s of (+)-2 are transformation of B-6 (7) to the chloride (3d) and construct ion of three cw-amino acid chains by utilizing (R)-(-)-Schollkopf's reagent (4), Wittig reagent (R)-(-)-5, and iodide (S)-(-)-6. (+)-Dpd (2) is a degr adation product of bone collagen and has been found to be a useful marker f or diagnosis of osteoporosis and other metabolic bone diseases. (C) 2000 El sevier Science Ltd. All rights reserved.