Journal article
Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: formal synthesis of quinine
Organic & biomolecular chemistry, Vol.9(11), pp.4039-4043
06/07/2011
DOI: 10.1039/c1ob05219e
PMCID: PMC4114234
PMID: 21537510
Abstract
Stereocontrolled Mn-mediated radical addition of alkyl iodides to chiral N-acylhydrazones enables strategic C-C bond disconnection of chiral amines. This strategy was examined in the context of a total synthesis of quinine, generating new findings of functional group compatibility leading to a revised strategy. Completion of a formal synthesis of quinine is presented, validating the application of Mn-mediated radical addition as a useful new C-C bond construction method for alkaloid synthesis. The Mn-mediated addition generates the chiral amine substructure of quinine with complete stereocontrol. Subsequent elaboration includes two successive ring closures to forge the azabicyclo[2.2.2]octane ring system of quincorine, linked to quinine through two known reactions.
Details
- Title: Subtitle
- Intermolecular radical addition to N-acylhydrazones as a stereocontrol strategy for alkaloid synthesis: formal synthesis of quinine
- Creators
- Gregory K Friestad - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA. gregory-friestad@uiowa.eduAn JiChandra Sekhar KorapalaJun Qin
- Resource Type
- Journal article
- Publication Details
- Organic & biomolecular chemistry, Vol.9(11), pp.4039-4043
- DOI
- 10.1039/c1ob05219e
- PMID
- 21537510
- PMCID
- PMC4114234
- NLM abbreviation
- Org Biomol Chem
- ISSN
- 1477-0520
- eISSN
- 1477-0539
- Publisher
- England
- Grant note
- R01 GM067187 / NIGMS NIH HHS R01-GM67187 / NIGMS NIH HHS
- Language
- English
- Date published
- 06/07/2011
- Academic Unit
- Chemistry
- Record Identifier
- 9983985814802771
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