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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 alpha-amino acid chains by utilizing (R)-(-)-Schollkopf’s reagent (4), Wittig reagent (R)-(-)-5, and iodide (5)-(-)-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. (C) 2000 Elsevier Science Ltd.
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI