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Issue 9, 2012
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A chemical synthesis of 11-methoxy mitragyninepseudoindoxyl featuring the interrupted Ugi reaction

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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.

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

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Supplementary files

Article information


Submitted
25 May 2012
Accepted
26 Jun 2012
First published
04 Jul 2012

Chem. Sci., 2012,3, 2849-2852
Article type
Edge Article

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

J. Kim, J. S. Schneekloth and E. J. Sorensen, Chem. Sci., 2012, 3, 2849
DOI: 10.1039/C2SC20669B

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