386285-44-5Relevant academic research and scientific papers
Total synthesis of (±)-decinine via an oxidative biaryl coupling with defined axial chirality
Shan, Zhen-Hua,Liu, Ji,Xu, Ling-Min,Tang, Ye-Feng,Chen, Jia-Hua,Yang, Zhen
, p. 3712 - 3715 (2012/09/21)
The total synthesis of (±)-decinine has been achieved. The key steps in the synthesis involved the formation of lasubine II via a gold catalyzed annulation of 1-(but-3-yn-1-yl)piperidine and the formation of the 12-membered ring of decinine (1) with complementary atropselectivity via a VOF 3-mediated oxidative biaryl coupling reaction.
Enantiodivergent synthetic entry to the quinolizidine alkaloid lasubine II
Saha, Nemai,Biswas, Tanmoy,Chattopadhyay, Shital K.
, p. 5128 - 5131 (2011/12/05)
Intramolecular cycloaddition of the syn- and the anti-nitrone 9 and 13 leads stereoselectively to the azabicyclic compounds 10 and 14 which may provide access to both enantiomers of the quinolizidine alkaloid lasubine II.
A modular, efficient, and stereoselective synthesis of substituted piperidin-4-ols
Cui, Li,Li, Chaoqun,Zhang, Liming
supporting information; experimental part, p. 9178 - 9181 (2011/02/28)
The pied piper-idinol of Hamelin: The one-pot synthesis of piperidin-4-ols by sequential gold-catalyzed cyclization, chemoselective reduction, and spontaneous Ferrier rearrangement has a broad substrate scope and shows excellent diastereoselectivity in th
An enantioselective organocatalytic approach to both enantiomers of lasubine II
Verkade, Jorge M.M.,Van Der Pijl, Ferdi,Willems, Marian M.J.H.P.,Quaedflieg, Peter J.L.M.,Van Delft, Floris L.,Rutjes, Floris P.J.T.
supporting information; experimental part, p. 3207 - 3210 (2009/08/08)
A concise stereoselective route providing access to both enantiomers of the bioactive quinolizidine alkaloid lasubine II has been developed. The enantioselectivity was introduced by taking advantage of a proline-catalyzed asymmetric Mannich reaction. Next, the bicyclic system was constructed via a diastereoselective Mannich cyclization and subsequent ring-closing metathesis as the key steps.
Stereoselective synthesis of quinolizidine alkaloids: (-)-Lasubin II
Weymann, Markus,Kunz, Horst
experimental part, p. 425 - 430 (2009/01/31)
Based on a higly diastereoselective Mannich reaction of N-(3,4-dimethoxybenzylidene) 2,3,4,6-tetra-O-pivaloyl-β-D- galactopyranosylamine 3 with the Danishefsky diene the quinolizidine alkaloid lasubin II was synthesized in enantiomerically pure form in six steps.
Synthetic study of (-)-lasubine II via sequential cyclization process
Lim, Jaebum,Kim, Guncheol
, p. 88 - 89 (2008/09/17)
A new synthetic pathway to lythraceae alkaloid lasubine II has been developed. In this approach, we designed a sequential cyclization pathway for the formation of quinolizidine ring. For the preparation of the requisite precursor, a known chiral β-amino e
Ring Expansive Routes to Quinolizidine Alkaloids: Formal Synthesis of (-)-Lasubine II
Gracias, Vijaya,Zeng, Yibin,Desai, Pankaj,Aube, Jeffrey
, p. 4999 - 5001 (2007/10/03)
(Equation presented) The application of two nitrogen ring expansion reactions to lasubine alkaloid synthesis is reported. The approach involves a conjugate reduction/ alkylation sequence carried out on triisopropylsilyl- protected (S)-4-(-)-hydroxycyclopentenone, the formation of the quinolizidone ring system through nitrogen ring expansion, and the addition of an arylmetallic species to the resulting lactam. This work resulted in the preparation of 2-epA-lasubine II and a formal synthesis of lasubine II.
Two-component method to enantiopure quinolizidinones and Indolizidinones. Total synthesis of (-)-lasubine II.
Ma,Zhu
, p. 3927 - 3929 (2007/10/03)
The reaction of iodides 1 and enantiopure beta-amino esters 2 mediated by potassium carbonate in acetonitrile at 65 degrees C provides quinolizidinones or indolizidinones 3, together with piperidines or pyrrolidines 4. Hydrolysis of 4 to the corresponding
