Stereochemical issues related to the synthesis and reactivity of pyrazino[20 ,10 -5,1]pyrrolo[2,3-b]indole-1,4-diones
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1998
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Pergamon
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Caballero E, Avendaño C, Menéndez JC. Stereochemical issues related to the synthesis and reactivity of pyrazino[2′,1′-5,1]pyrrolo[2,3-b]indole-1,4-diones. Tetrahedron: Asymmetry. marzo de 1998;9(6):967-81. doi:10.1016/S0957-4166(98)00068-8
Abstract
The cyclization of all four diastereoisomers of cyclo-(Trp-Ala) to the corresponding 3,5a,6,10b,11,11ahexahydro-2H-pyrazino[20 ,10 -5,1]pyrrolo[2,3-b]indoles is studied from the stereochemical point of view. Epimerization of the tryptophan stereocenter during the cyclization and during acylation reactions of the N-2 atom of the tetracyclic derivatives is discussed.