A concise approach to tetracyclic spiroamine scaffold of erythrinan alkaloids via an oxidative dearomatization-spirocyclization sequence

Emi Saito, Nakamura Akihiko, Masahisa Nakada

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    Abstract

    This paper describes a novel synthetic approach to 11,12-dimethoxy-8,9-dihydro-1H-indolo[7a,1-a]isoquinoline-2,6-dione, which is a key synthetic intermediate to some erythrinan alkaloids. This concise approach features an oxidative dearomatization-spirocyclization sequence mediated by phenyliodine (III) bis(trifluoroacetate) (PIFA) that efficiently forms the tetracyclic spiroamine scaffold. An unusual solvent effect in the oxidative dearomatization-spirocyclization sequence is also described.

    Original languageEnglish
    Pages (from-to)1387-1395
    Number of pages9
    JournalHeterocycles
    Volume90
    Issue number2
    DOIs
    Publication statusPublished - 2015

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    ASJC Scopus subject areas

    • Analytical Chemistry
    • Organic Chemistry
    • Pharmacology

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