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Model Studies to Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization-Cope or Cyclopropanation-Cope Rearrangements as Key Steps

Roizen, Jennifer L. and Jones, Amanda C. and Smith, Russell C. and Virgil, Scott C. and Stoltz, Brian M. (2017) Model Studies to Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization-Cope or Cyclopropanation-Cope Rearrangements as Key Steps. Journal of Organic Chemistry, 82 (24). pp. 13051-13067. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20171107-103337734

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Abstract

Recently, we reported a convergent cyclopropanation–Cope approach to the core of ineleganolide, which was the first disclosed synthesis of the core of the norditerpene natural product ineleganolide. In this complementary work, a model system for the core of ineleganolide has been prepared through a series of tandem cyclopropanation–Cope and translactonization–Cope rearrangements. Work with this model system has enriched our understanding of the cyclopropanation–Cope rearrangement sequence. Additionally, research into this model system has driven the development of tandem translactonization–Cope rearrangements.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.joc.7b02030DOIArticle
http://pubs.acs.org/doi/10.1021/acs.joc.7b02030PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.joc.7b02030PublisherSupporting Information
ORCID:
AuthorORCID
Roizen, Jennifer L.0000-0002-6053-5512
Jones, Amanda C.0000-0001-8426-8407
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2017 American Chemical Society. Received: August 11, 2017; Published: November 7, 2017. The authors wish to thank the NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. Additionally, the authors gratefully acknowledge Larry Henling and the late Dr. Michael Day (Caltech) for X-ray crystallographic structural determination; Dr. Mona Shahgholi and Naseem Torian (Caltech) for mass spectrometric analysis; Dr. David VanderVelde (Caltech) for NMR experimental assistance and helpful discussions; Dr. Masaki Seto, Dr. N. Sherden, and Dr. D. E. White for helpful discussions; and Dr. R. A. Craig, II for editorial suggestions. J.L.R. thanks the California Tobacco-Related Disease Research Program of the University of California, Grant Number 14DT-0004 for a predoctoral fellowship. A.C.J. thanks the NIH (F32GM082000) for a postdoctoral fellowship. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
California Tobacco-Related Disease Research Program14DT-0004
NIH Postdoctoral FellowshipF32GM082000
Issue or Number:24
Record Number:CaltechAUTHORS:20171107-103337734
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20171107-103337734
Official Citation:Model Studies To Access the [6,7,5,5]-Core of Ineleganolide Using Tandem Translactonization–Cope or Cyclopropanation–Cope Rearrangements as Key Steps. Jennifer L. Roizen, Amanda C. Jones, Russell C. Smith, Scott C. Virgil, and Brian M. Stoltz. The Journal of Organic Chemistry 2017 82 (24), 13051-13067. DOI: 10.1021/acs.joc.7b02030
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:83027
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:07 Nov 2017 18:41
Last Modified:09 Mar 2020 13:19

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