112462-87-0Relevant academic research and scientific papers
A synthesis of 5-hydroxysedamine using hydroformylation
Bates, Roderick W.,Aslam, Nur Filza Bte Mohamed,Tang, Chi H.,Simon, Oliver
, p. 2134 - 2140 (2014/03/21)
A synthesis of 5-hydroxysedamine, a Sedum alkaloid, has been completed using N,O-heterocycle chemistry to establish the aminoalcohol structure, hydroformylation to form the piperidine ring and diastereoselective dihydroxylation to introduce the 5-hydroxy group.
Asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine based on a cis-diastereoselective 1,4-asymmetric induction
Liu, Gang,Meng, Jie,Feng, Chen-Guo,Huang, Pei-Qiang
, p. 1297 - 1303 (2008/12/20)
The asymmetric syntheses of (-)-epi-pseudoconhydrine and (-)-5-hydroxysedamine are reported. The key to these syntheses is an unusual highly cis-diastereoselective 1,4-asymmetric induction in the α-amidoallylation of the new chiral building block 15.
Synthesis of β-hydroxypiperidine alkaloids by anodic oxidation of carbamates and hydroboration
Plehiers, Mark,Hootelé, Claude
, p. 2444 - 2453 (2007/10/03)
The β-hydroxypiperidine alkaloids (±)-pseudoconhydrine, (±)-N-methylpseudoconhydrine, (-)-5-hydroxysedamine, and (+)-sedacryptine were synthesized. Successive functionalization of the piperidine ring via anodic methoxylation allowed the regio- and stereos
Synthesis of (+)- and (-)-Hydroxysedamine and (+)-N-Methylpseudoconhydrine from (S)-Glutamic Acid via Homochiral Acyliminium Ion
Herdeis, Claus,Held, Walter A.,Kirfel, Armin,Schwabenlaender, Franz
, p. 1295 - 1302 (2007/10/02)
Efficient syntheses of (+)-N-methylpseudoconhydrine (5) and (-)-hydroxysedamine (10) are described starting from the readily available (2RS,5S)-Methyl 5-(tert-butyldimethylsilyloxy)-2-ethoxypiperidine-1-carboxylate (1) and proceeding via homochiral acylim
Hydroboration of Enecarbamates and the Synthesis of β-Hydroxypiperidine Alkaloids
Plehiers, Mark,Hootele, Claude
, p. 7569 - 7570 (2007/10/02)
The β-hydroxypiperidine alkaloids 5, 6 and 8 were diastereoselectively synthesized using hydroboration of enecarbamates 2b-c as a key step.
SEDUM ALKALOIDS. X. STRUCTURE AND SYNTHESIS OF NEW 3- AND 5-HYDROXYPIPERIDINE ALKALOIDS.
Ibebeke-Bomangwa, W.,Hootele, C.
, p. 935 - 945 (2007/10/02)
The structure and absolute configuration of (-)-3-hydroxynorallosedamine 1, (-)-3-hydroxyallosedamine 2 and (-)-5-hydroxysedamine 3, three new minor alklaloids isolated from Sedum acre, are reported.A nitrone-based synthesis of the new bases is described.
