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

5 Citations (Scopus)

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

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Pactamycin
Amination
Alkenes
Biological Products
Nitrogen
Hydroxylation
Carbamates
Functional groups
Catalysis
Anions
Esters
Carbon
Oxygen

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthetic Studies Toward Pactamycin Highlighting Oxidative C-H and Alkene Amination Technologies. / Su, Justin Y.; Olson, David; Ting, Stephen I.; Du Bois, J.

In: Journal of Organic Chemistry, Vol. 83, No. 13, 06.07.2018, p. 7121-7134.

Research output: Contribution to journalArticle

Su, Justin Y. ; Olson, David ; Ting, Stephen I. ; Du Bois, J. / Synthetic Studies Toward Pactamycin Highlighting Oxidative C-H and Alkene Amination Technologies. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 13. pp. 7121-7134.
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