The Synthesis of Melohenine B and a Related Natural Product

Christopher Stuart Lancefield, Linna Zhou, Tomas Lebl, Alexandra Martha Zoya Slawin, Nicholas James Westwood

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.

Original languageEnglish
Pages (from-to)6166-6169
Number of pages4
JournalOrganic Letters
Volume14
Issue number24
DOIs
Publication statusPublished - 21 Dec 2012

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