Synthesis of (+)-Kuraramine

Frigerio, Francesco; Haseler, Claire A.; Gallagher, Timothy

doi:10.1055/s-0029-1219377

Synlett

2010

DOI: 10.1055/s-0029-1219377

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Synthesis of (+)-Kuraramine

Francesco Frigerio¹,

Claire A. Haseler²,

Timothy Gallagher³

Abstract: The first synthesis of (+)-kuraramine via oxidative cleavage of (-)-N-methylcytisine is reported. An alternative but unsuccessful approach to (+)-kuraramine is also described based on extending an intramolecular enolate addition protocol that had previously been applied successfully to cytisine.

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Cited by 3 publications

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The Role of Halogen Bonding in Crystal Structures of 3-Halogeno Cytisine Derivatives

Przybył

Kubicki

2012

J Chem Crystallogr

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The crystal structures of three 3-halogeno derivatives of 13N-substituted cytisine have been determined by X-ray diffraction. The two 13-acetyl substituted compounds, 3-bromo (1) and 3-iodo (2) are isostructural, with the isostructurality index as high as 99%. They both crystallize in monoclinic P2 1 space group, with unit cell parameters of a = 8.4709(10) Å , b = 9.2266(12) Å , c = 8.6051(10) Å , b = 98.528 (11)8 (1) and a = 8.2322(6) Å , b = 9.1724(7) Å , c = 8.5494(6) Å , b = 98.181 (7)8 (2). In turn, 3-bromo-13-t-butyl-carbonate derivative (3) crystallizes in orthorhombic P2 1 2 1 2 1 space group with a = 6.8171(3) Å , b = 7.8994(4) Å , c = 31.4657(15) Å . Conformation of the cytisine skeleton is similar in all three molecules, with almost planar A ring, sofa conformation of B-ring and C ring being an almost ideal chair. However, the orientations of the double C=O bonds in 13N-substituents are completely different: in 1 and 2 it is cis with respect to C12 (C12-N13-C14-O15 torsion angle is 3.3(4)8 in 1 and 1.3(6)8 in 2) while in 3 it is trans (-175.4(3)8). In the structures of 1 and 2 the driving force of the crystal architecture are quite strong C-HÁÁÁX halogen bonds with CÁÁÁX distances far shorter than the sums of van der Waals radii (CÁÁÁBr in 1 is 2.9430(19) Å and CÁÁÁI in 2 2.974(3)). In contrast in 3-partially as the consequence of different orientation of the substituent-there are no halogen bondings but instead some weak C-HÁÁÁO contacts organize the molecules into two-dimensional patterns.

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The Role of Halogen Bonding in Crystal Structures of 3-Halogeno Cytisine Derivatives

Przybył

Kubicki

2012

J Chem Crystallogr

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Solvent-free synthesis of cytisine-thienopyrimidinone conjugates via transannulation of 1H-tetrazoles: Crystal and molecular structure, docking studies and screening for anticancer activity

Pokhodylo

Shyyka

Slyvka

et al. 2021

Journal of Molecular Structure

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Oxidative Fragmentation of Cytisine as an Entry to the Bis(piperidine) Scaffold of Virgidivarine

Gallagher¹,

Niwetmarin²

2022

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Synthesis of (+)-Kuraramine

Cited by 3 publications

References 5 publications

The Role of Halogen Bonding in Crystal Structures of 3-Halogeno Cytisine Derivatives

The Role of Halogen Bonding in Crystal Structures of 3-Halogeno Cytisine Derivatives

Solvent-free synthesis of cytisine-thienopyrimidinone conjugates via transannulation of 1H-tetrazoles: Crystal and molecular structure, docking studies and screening for anticancer activity

Oxidative Fragmentation of Cytisine as an Entry to the Bis(piperidine) Scaffold of Virgidivarine

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