Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids.
A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C(6) olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids.
Alibés
Ramon
R
Departament de Química and Unitat de Cristallografia, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
Blanco
Pilar
P
Casas
Eva
E
Closa
Montserrat
M
de March
Pedro
P
Figueredo
Marta
M
Font
Josep
J
Sanfeliu
Elena
E
Alvarez-Larena
Angel
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D041901:Stemonaceae / Q000737:chemistry*
D000470:Alkaloids