310904-19-9

Upstream product

• 14447-18-8 benzyl 2-cyanoacetate 
• 257883-80-0 (S)-2-[bis(tert-butoxycarbonyl)amino]-6-hydroxyhexanoic acid tert-butyl ester 
• 226985-05-3 (S)-(-)-1-tert-butyl-2--5-hexenoate 
• 147590-65-6 2-benzyl 3,4-diethyl-1H-pyrrole-2-carboxylate 
• 257883-70-8 (S)-2-[bis(tert-butoxycarbonyl)amino]-6-iodohexanoic acid tert-butyl ester 

Relevant academic research and scientific papers

Bone collagen cross-links: A convergent synthesis of (+)-deoxypyrrololine

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.