Tetrahedron

Collagen cross-links: Synthesis of pyridinoline, deoxypyridinoline and their analogues

M Adamczyk, DD Johnson, RE Reddy

Index: Adamczyk, Maciej; Johnson, Donald D.; Reddy, Rajarathnam E. Tetrahedron, 1999 , vol. 55, # 1 p. 63 - 88

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Citation Number: 41

Abstract

An efficient chiral synthesis of (S, S)-(−)-3g, a key intermediate for the preparation of collagen cross-links pyridinoline (Pyd, 1) and deoxypyridinoline (Dpd, 2) was achieved from (4S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl) amino]-5-oxopentanoic acid (21b). Quaternization of (S, S)-(−)-3g with iodide (2S, 5R)-(+)-4a followed by hydrolysis provided a first chiral synthesis of natural (+)-Pyd (1). 1-(2S)-(+)-Pyd (1) was also synthesized from (S, ...