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Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol

Bagdanoff, Jeffrey T. and Behenna, Douglas C. and Stockdill, Jennifer L. and Stoltz, Brian M. (2016) Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol. European Journal of Organic Chemistry, 2016 (12). pp. 2101-2104. ISSN 1434-193X . PMCID PMC5225988. https://resolver.caltech.edu/CaltechAUTHORS:20160425-132914132

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Abstract

The enantioselective synthesis of both caprolactam and enone synthons for the DEFG ring system of zoanthenol are described. The evolution of this approach proceeds first through a synthesis using the chiral pool as a starting point. Challenges in protecting-group strategy led to the modification of this approach beginning with (±)-glycidol. Ultimately, an efficient approach was developed by employing an asymmetric hetero-Diels–Alder reaction. The caprolactam building block can be converted by an interesting selective Grignard addition into the corresponding enone synthon. Addition of a model alkyne provides support for the late-stage addition of a hindered alkyne to the caprolactam building block.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/ejoc.201600223DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600223/abstractPublisherArticle
http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600223/suppinfoPublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5225988/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: February 26, 2016; Article first published online: 19 APR 2016. The authors wish to thank the NIH-NIGMS (R01GM080269), the Tobacco Related Disease Research Program (Fellowship to J. T. B.), the John and Fannie Hertz Foundation (predoctoral fellowship to D. C. B.), Novartis (predoctoral fellowship to J. L. S.), the Philanthropic Education Organization (Scholar Award to J. L. S.), and Abbott, Amgen, Boehringer-Ingelheim, Bristol-Myers Squibb, Merck, and Caltech for their generous financial support. The authors thank Professor Karl Scheidt (Northwestern) for helpful early discussions.
Funders:
Funding AgencyGrant Number
NIHR01GM080269-01
California Tobacco-Related Disease Research ProgramUNSPECIFIED
Fannie and John Hertz FoundationUNSPECIFIED
NovartisUNSPECIFIED
Philanthropic Education OrganizationUNSPECIFIED
AbbottUNSPECIFIED
AmgenUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
MerckUNSPECIFIED
CaltechUNSPECIFIED
Subject Keywords:Zoanthamines; Zoanthenol; Enantioselectivity; Hetero-Diels–Alder reaction; Allylation
Issue or Number:12
PubMed Central ID:PMC5225988
Record Number:CaltechAUTHORS:20160425-132914132
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160425-132914132
Official Citation:Bagdanoff, J. T., Behenna, D. C., Stockdill, J. L. and Stoltz, B. M. (2016), Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol. Eur. J. Org. Chem., 2016: 2101–2104. doi: 10.1002/ejoc.201600223
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66457
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:02 May 2016 21:25
Last Modified:03 Oct 2019 09:56

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