A chemical synthesis of 11-methoxy mitragynine pseudoindoxyl featuring the interrupted Ugi reaction

Jimin Kim, John S. Schneekloth, Erik J. Sorensen

Research output: Contribution to journalArticle

33 Scopus citations

Abstract

A synthesis of 11-methoxy mitragynine pseudoindoxyl, a new member of the mitragynine class of opioid agonists, from a derivative of the Geissman-Waiss lactone is described. An internal attack of an electron-rich aromatic ring on an electrophilic nitrilium ion and a late-stage construction of the functionalized piperidine ring by the method of reductive cyclization are the pivotal transformations; both ring annulations proceed in a highly diastereoselective fashion. The construction of substituted indoxyl frameworks by the interrupted Ugi method offers an attractive alternative to the strategy of oxidatively rearranging indoles.

Original languageEnglish (US)
Pages (from-to)2849-2852
Number of pages4
JournalChemical Science
Volume3
Issue number9
DOIs
StatePublished - Sep 2012

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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