184535-16-8Relevant academic research and scientific papers
N-tert -Butanesulfinyl Imines in Alkaloid Synthesis: Stereoselective Synthesis of (R)-Coniine and Formal Synthesis of (S)-Coniceine 1
Damodar, Kongara,Lingaiah, Maram,Bhunia, Nisith,Das, Biswanath
, p. 2478 - 2482 (2011/09/16)
A stereoselective synthesis of the hemlock alkaloid (R)-coniine and a formal synthesis of the indolizidine alkaloid (S)-δ-coniceine were achieved by means of a highly diastereoselective Barbier-type indium-mediated allylation strategy involving (S)-(N-ter
Enantioselective organocatalytic intramolecular aza-Michael reaction: A concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine
Fustero, Santos,Jimenez, Diego,Moscardo, Javier,Catalan, Silvia,Del Pozo, Carlos
, p. 5283 - 5286 (2008/09/18)
(Chemical Equation Presented) The intramolecular aza-Michael reaction of carbamates bearing remote α,β-unsaturated aldehydes under organocatalytic conditions took place with good yields and excellent ee's when Jorgensen catalyst IV was used in the process, giving rise to the enantioselective formation of several five- and six-membered heterocycles. The developed methodology was applied to the synthesis of three piperidine alkaloids.
Asymmetric synthesis of (+)-febrifugine and (+)-isofebrifugine using yeast reduction
Takeuchi, Yasuo,Azuma, Kumiko,Takakura, Kentaro,Abe, Hitoshi,Kim, Hye-Sook,Wataya, Yusuke,Harayama, Takashi
, p. 1213 - 1218 (2007/10/03)
The antimalarial agents febrifugine (D-1) and isofebrifugine (D-2) were synthesized from chiral 3-piperidinol (D-4), which was asymmetrically prepared by the yeast reduction of 3-piperidone derivatives (DL-3), with dynamic optical resolution.
A new asymmetric entry to 2-substituted piperidines. A concise synthesis of (+)-coniine, (-)-pelletierine, (+)-δ-coniceine, and (+)-epidihydropinidine
Takahata, Hiroki,Kubota, Minoru,Takahashi, Seiki,Momose, Takefumi
, p. 3047 - 3054 (2007/10/03)
A new asymmetric route to 2-substituted piperidines involving the Sharpless asymmetric dihydroxylation (AD) of 5-hexenylazide 1 and an intramolecular aminocyclization as crucial steps and its application to the asymmetric synthesis of four piperidine alkaloids, (+)-coniine 2, (-)-pelletierine 3, (+)-δ-coniceine 4, aND (+)-epidihydropinidine 5 is presented.
Diastereofacial Selectivity in Intermolecular Nitrone Cycloadditions to Chiral Allyl Ethers. Application to Chiral Synthesis of Coniine
Ito, Masayuki,Maeda, Masae,Kibayashi, Chihiro
, p. 3765 - 3768 (2007/10/02)
The intermolecular cycloadditions of a cyclic nitrone to chiral allyl ethers take place with erythro selectivity, where the degree of selectivity achieved is dependent upon the size of the alkyl substituent attached to the allylic chiral center, and these reactions are applied to the synthesis of optically active alkaloid coniine.
