Biomimetic total synthesis of the pentacyclic Amaryllidaceae alkaloid derivative gracilamine

Nadia Gao, Martin G. Banwell*, Anthony C. Willis

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    27 Citations (Scopus)

    Abstract

    The illustrated azomethine ylide, produced through a Schiff base condensation of the corresponding aldehydecontaining C3a-arylhexahydroindole with ethyl L-leucinate, engages in a stereoselective intramolecular cycloaddition reaction to give adduct 23 that has been elaborated, over eight steps, into the racemic modification of the alkaloid derivative gracilamine (1). The formation of this ylide and its conversion into isomer 23 mimics the proposed biogenesis of the pentacyclic framework of compound 1.

    Original languageEnglish
    Pages (from-to)162-165
    Number of pages4
    JournalOrganic Letters
    Volume19
    Issue number1
    DOIs
    Publication statusPublished - 6 Jan 2017

    Fingerprint

    Dive into the research topics of 'Biomimetic total synthesis of the pentacyclic Amaryllidaceae alkaloid derivative gracilamine'. Together they form a unique fingerprint.

    Cite this