134457-92-4Relevant academic research and scientific papers
Total syntheses of heliotridane and pseudoheliotridane through nitrodiene–acrylate 6π-electrocyclization/[3+2] cycloaddition
Koc, Esra,Kwon, Ohyun
, p. 4195 - 4200 (2017/06/29)
The total syntheses of the pyrrolizidine alkaloids heliotridane and pseudoheliotridane have been accomplished in six steps (overall yields: 24 and 7%, respectively) using, for the first time, the tandem 6π-electrocyclization/[3+2] dipolar cycloaddition of
Hydrogenation of pyrrolizin-3-ones; New routes to pyrrolizidines
Despinoy, Xavier L. M.,McNab, Hamish
experimental part, p. 4502 - 4511 (2009/12/25)
Pyrrolizin-3-ones (e.g.1) can be easily hydrogenated to their hexahydro (pyrrolizidin-3-one) derivatives in the presence of heterogeneous catalysts. Good diastereoselectivity (up to >97:3, depending on catalysts and solvent) can be achieved if the pyrroli
Stereoselective synthesis of (7aS)-1-methylenehexahydro-1H-pyrrolizine and (-)-heliotridane from N-diphenylmethyl-(S)-proline ethyl ester
Lysenko,Kulinkovich
, p. 70 - 74 (2007/10/03)
Alkaloid (7aS)-1-methylenehexahydro-1H-pyrrolizine was synthesized from N-diphenylmethyl-(S)-proline ethyl ester by cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium tetraisopropoxide, replacement of the protectin
Synthesis of (±)-pseudoheliotridane by allylboration of 1-pyrroline
Gurskii,Potapova,Bubnov
, p. 1410 - 1412 (2007/10/03)
Reaction of tricrotylborane with 1-pyrroline proceeds stereoselectively to give (1R*, 1′S*)-2-(1-methylallyl)pyrrolidine. The latter was converted to the pyrrolizidine alkaloid (±)-pseudoheliotridane through hydroboration - oxidation - intramolecular cycl
Enantioselective Total Synthesis of Indolizidine Alkaloids (-)-205A and (-)-235B
Polniaszek, Richard P.,Belmont, Stephen E.
, p. 4868 - 4874 (2007/10/02)
Enantioselective total syntheses of indolizidine alkaloids (-)-205A and (-)-235B are described.The syntheses proceed via a common late-stage intermediate, α-aminonitrile 1.Absolute stereochemical control over the C8 and C8a stereocenters in these material
