Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cylindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C)

Artigo Revisado por pares

Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cylindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C)

1997; Elsevier BV; Volume: 38; Issue: 19 Linguagem: Inglês

10.1016/s0040-4039(97)00632-1

ISSN

1873-3581

Autores

William H. Pearson, Nancy S. Barta, Jeff W. Kampf,

Tópico(s)

Asymmetric Synthesis and Catalysis

Resumo

Tin-lithium exchange of 13 with n-BuLi produced the 2-azapentadienyl anion 6 (R = CH3), which participated in a [π4s+π2s] cycloaddition reaction with phenyl vinyl sulfide to afford the spirocyclic pyrrolidine 14, which as coverted to 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C) 17 by a sequence of steps involving oxidative cleavage of the propenyl side-chain, intramolecular reductive amination, and desulfurization.

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Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cylindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C)