473893-67-3

Upstream product

• 888745-46-8 (R)-Undeca-1,10-diene-4,8-diol 
• 111512-38-0 4,8-dihydroxy-1,10-undecanediene 
• 100-46-9 benzylamine 
• 958003-20-8 C₂₅H₃₂O₆S₂ 

Downstream Products

• 473893-73-1 tert-butyl (2S,6S)-8-(2-oxopropyl)-2-prop-2-enylpiperidinecarboxylate 
• 28720-60-7 (2R,6R)-(-)-2-methyl-6-undecylpiperidine 
• 888745-54-8 (S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-2-ol 

Relevant academic research and scientific papers

A new route to trans-2,6-disubstituted piperidine-related alkaloids using a novel C2-symmetric 2,6-diallylpiperidine carboxylic acid methyl ester

A novel C2-symmetric 2,6-diallylpiperidine carboxylic acid methyl ester 1 was prepared by the double asymmetric allylboration of glutaldehyde followed by an aminocyclization and carbamation. On the basis of desymmetrization of 1 using iodocarbamation, one allyl group of 1 was protected and monofunctionalizations of the resulting oxazolidinone 11 were performed. The reaction of the N-methoxycarbonyl piperidine 25 employing decarbamation reagent (n-PrSLi or TMSI) as a key step gave oxazolidinone 26 or 17 including an intramolecular ring formation, which was transformed in a few steps into (-)-porantheridine (2) and (-)-2-epi-porantheridine (3), respectively. In addition, the expedient synthesis of (+)-epi-dihydropinidine (4), (2R,6R)-trans-solenopsin A (5), and precoccinelline (6), starting from 11 is described. The Royal Society of Chemistry 2006.

A novel C(2)-symmetric 2,6-diallylpiperidine carboxylic acid methyl ester as a promising chiral building block for piperidine-related alkaloids.

C(2)-symmetric 2,6-diallylpiperidine 1-carboxylic acid methyl ester (5) was examined via the double asymmetric allylboration of glutaraldehyde followed by aminocyclization and carbamation as a promising chiral building block for piperidine-related alkaloids, which were synthesized by the desymmetrization of 5 using intramolecular iodocarbamation as a key step. [reaction: see text]