Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems

Handle URI:
http://hdl.handle.net/10754/599838
Title:
Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems
Authors:
Bennett, Nathan B.; Hong, Allen Y.; Harned, Andrew M.; Stoltz, Brian M.
Abstract:
A general method for the synthesis of β-substituted and unsubstituted cycloheptenones bearing enantioenriched all-carbon γ-quaternary stereocenters is reported. Hydride or organometallic addition to a seven-membered ring vinylogous ester followed by finely tuned quenching parameters achieves elimination to the corresponding cycloheptenone. The resulting enones are elaborated to bi- and tricyclic compounds with potential for the preparation of non-natural analogs and whose structures are embedded in a number of cycloheptanoid natural products.
Citation:
Bennett NB, Hong AY, Harned AM, Stoltz BM (2012) Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems. Org Biomol Chem 10: 56–59. Available: http://dx.doi.org/10.1039/c1ob06189e.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Org. Biomol. Chem.
KAUST Grant Number:
KUS-11-006-02
Issue Date:
2012
DOI:
10.1039/c1ob06189e
PubMed ID:
22009489
PubMed Central ID:
PMC3365663
Type:
Article
ISSN:
1477-0520; 1477-0539
Sponsors:
This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. AMH thanks the NIH for a postdoctoral fellowship. Materia, Inc. is gratefully acknowledged for the donation of catalysts. Michael Krout, Thomas Jensen, Christopher Henry, Scott Virgil, and Sarah Reisman are acknowledged for helpful discussions. David VanderVelde is acknowledged for critical NMR support.
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Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorBennett, Nathan B.en
dc.contributor.authorHong, Allen Y.en
dc.contributor.authorHarned, Andrew M.en
dc.contributor.authorStoltz, Brian M.en
dc.date.accessioned2016-02-28T06:11:01Zen
dc.date.available2016-02-28T06:11:01Zen
dc.date.issued2012en
dc.identifier.citationBennett NB, Hong AY, Harned AM, Stoltz BM (2012) Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems. Org Biomol Chem 10: 56–59. Available: http://dx.doi.org/10.1039/c1ob06189e.en
dc.identifier.issn1477-0520en
dc.identifier.issn1477-0539en
dc.identifier.pmid22009489en
dc.identifier.doi10.1039/c1ob06189een
dc.identifier.urihttp://hdl.handle.net/10754/599838en
dc.description.abstractA general method for the synthesis of β-substituted and unsubstituted cycloheptenones bearing enantioenriched all-carbon γ-quaternary stereocenters is reported. Hydride or organometallic addition to a seven-membered ring vinylogous ester followed by finely tuned quenching parameters achieves elimination to the corresponding cycloheptenone. The resulting enones are elaborated to bi- and tricyclic compounds with potential for the preparation of non-natural analogs and whose structures are embedded in a number of cycloheptanoid natural products.en
dc.description.sponsorshipThis publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. AMH thanks the NIH for a postdoctoral fellowship. Materia, Inc. is gratefully acknowledged for the donation of catalysts. Michael Krout, Thomas Jensen, Christopher Henry, Scott Virgil, and Sarah Reisman are acknowledged for helpful discussions. David VanderVelde is acknowledged for critical NMR support.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleSynthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systemsen
dc.typeArticleen
dc.identifier.journalOrg. Biomol. Chem.en
dc.identifier.pmcidPMC3365663en
dc.contributor.institutionThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, California Institute of Technology, Division of Chemistry and Chemical Engineering, Mail Code 101-20, Pasadena, CA 91125, USA.en
kaust.grant.numberKUS-11-006-02en
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