257883-82-2Relevant academic research and scientific papers
Total synthesis of (+)-deoxypyrrololine: A potential biochemical marker for diagnosis of osteoporosis
Adamczyk, Maciej,Johnson, Donald D.,Reddy, Rajarathnam E.
, p. 3537 - 3539 (1999)
The collagen cross-link (+)-deoxypyrrololine (Dpl, 1), a potential biochemical marker for diagnosis of osteoporosis, has been obtained by a general and convergent total synthesis. The key synthetic features involve utilization of a L-glutamic acid derivat
Bone collagen cross-links: A convergent synthesis of (+)-deoxypyrrololine
Adamczyk,Johnson,Reddy
, p. 11 - 19 (2007/10/03)
A convergent total synthesis of (+)-deoxypyrrololine (Dpl, 4), a putative cross-link of bone collagen, is described starting from a commercially available L-glutamic acid derivative, (4S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid (16). Condensation of aldehyde (S)-(-)-17 with nitro compound (S)-(-)-27, both of which were prepared from a common precursor (S)-16, gave the α-hydroxynitro compound 28, which upon acetylation afforded α-acetoxynitro compound 14 in good yield. Subsequent condensation and cyclization of α-acetoxynitro compound 14 with benzyl isocyanoacetate (15) in the presence of DBU in THF gave the key pyrrole intermediate (S,S)-(-)-12 in 57% yield. N-Alkylation of pyrrole (S,S)-(-)-12 with iodide (S)-(-)-13 using t-BuOK in THF afforded the 2-benzyloxycarbonyl-1,3,4-substituted pyrrole derivative (-)-29 in 42% yield. Removal of the protective groups in (-)-29 followed by hydrogenolysis and decarboxylation afforded the crosslink (+)-Dpl (4) in good overall yield. The synthesis of an analogue (S)-(+)-24 and formation of a novel tetrahydroindole derivative (-)-31 are also described.
