Synthesis of a New Phorbazole and Its Derivatives

I. Wayan Muderawan, Wendy A. Louglin, David J. Young

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.

    Original languageEnglish
    Pages (from-to)1395-1403
    Number of pages9
    JournalSynthesis (Germany)
    Volume54
    Issue number5
    Early online dateNov 2021
    DOIs
    Publication statusPublished - 2 Mar 2022

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