Artículos de revistas
Synthesis Of Indolizidines And Pyrrolizidines Through The [2 + 2]cycloaddition Of Five-membered Endocyclic Enecarbamates To Alkyl Ketenes. Unusual Regioselectivity Of Baeyer-villiger Ring Expansions Of Alkyl Aza-bicyclic Cyclobutanones
Registro en:
Journal Of Organic Chemistry. , v. 67, n. 11, p. 3651 - 3661, 2002.
223263
10.1021/jo016189u
2-s2.0-0037204693
Autor
De Faria A.R.
Salvador E.L.
Correia C.R.D.
Institución
Resumen
The total systheses of two indolizidine skeletons and of the necine base (±)-platynecine were accomplished in a concise manner with good overall yields starting from a common five-membered endocyclic enecarbamate. These syntheses feature a (2 + 2)cycloaddition of the five-membered endocyclic enecarbamate 5 to alkykletenes that proceed in high yields and with high stereo-selectivity to provide an endo alkyl cycloadduct as the major or only product. The minor exo alkyl cycloadducts, which can be observed in some [2 +2]cycloadditions, seem to derive from the endo cycloadduct, the putative kinetic product, by epimerization. An unusual regioselectivity was observed for the Baeyer-Villiger oxidation is drastically reduced, leading to mixtures of regioselectivity of the Baeyer-Villager oxidation is drastically reduced, leading to mixtures of regioisomeric lactones in a ratio of ∼1.5 to 1. It is hypothesized that the steric strain built into the Criegee cyclobutane intermediate is the regioselectivity controlling factor in these oxidationas, overriding any stereoelectronic bias for ring expansion. A rationale for the mechanism of the [2 + 2]cycloaddition involving enecarbamates and ketenes is presented, which seems to involved the participation of an N-acyliminium-enolate intermediate. 67 11 3651 3661 Michael, J.P., (2001) Nat. Prod. Rep., 18, p. 520 Liddell, J.R., (2001) Nat. Prod. Rep., 18, p. 441 Harborne, J.B., (2001) Nat. Prod. Rep., 18, p. 361. , and references therein Goss, P.E., Reid, C.L., Bailey, D., Denis, J.W., (1997) Clin. Cancer. Res., 3, p. 1077 Goss, P.E., Baker, M.A., Carver, J.P., Denis, J.W., (1995) Clin. Cancer. Res., 1, p. 935 Hirota, H., Matsunaga, S., Fusetami, N., (1990) Tetrahedron Lett., 31, p. 4163 Berry, D.L., Schoofs, G.M., Molyneux, R.J., (1996) J. Nat. 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