A simple modular synthesis of pyridinoline a collagen cross-link of biochemical interest

A simple convergent synthesis of the collagen cross-link pyridinoline starting from glycine is reported.

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(2S,5R)-2-Benzyloxycarbonylamino-5-iodomethyl-δ-valerolactoneC14H16INO4[α]D25=+7.0 (c 1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,5R)

(2S,5S)-2-Benzyloxycarbonylamino-5-iodomethyl-δ-valerolactoneC14H16INO4[α]D25=+41.5 (c 1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S,5S)

(S)-2-Benzyloxycarbonylaminohex-5-enoic acidC14H17NO4Ee >98%[α]D25=+21.6 (c 1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S)

Allyl (2S)-2-benzyloxycarbonylamino-6-iodo-5-oxohexanoateC14H16INO5[α]D25=−3.0 (c 1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (2S)