Synthetic Studies Toward Pactamycin Highlighting Oxidative C-H and Alkene Amination Technologies

Justin Y. Su, David Olson, Stephen I. Ting, J. Du Bois

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

A strategy enabled by C-H and alkene amination technologies for synthesizing the aminocyclitol natural product, pactamycin, is disclosed. This work features two disparate approaches for assembling the five-membered ring core of the target, the first of which utilizes acyl anion catalysis and a second involving β-ketoester aerobic hydroxylation. Installation of the C3-N bond, one of three contiguous nitrogen centers, is made possible through Rh-catalyzed allylic C-H amination of a sulfamate ester. Subsequent efforts are presented to introduce the C1,C2 cis-diamino moiety en route to pactamycin, including carbamate-mediated alkene aziridination. In the course of these studies, assembly of the core of C2-epi-pactamycate, which bears the carbon skeleton and all of the requisite nitrogen and oxygen functional groups found in the natural product, has been achieved.

Original languageEnglish (US)
Pages (from-to)7121-7134
Number of pages14
JournalJournal of Organic Chemistry
Volume83
Issue number13
DOIs
StatePublished - Jul 6 2018
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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