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Synthesis of non-natural cyanthiwigin–gagunin hybrids through late-stage diversification of the cyanthiwigin natural product core

Kim, Kelly E. and Sakazaki, Yuka and Stoltz, Brian M. (2020) Synthesis of non-natural cyanthiwigin–gagunin hybrids through late-stage diversification of the cyanthiwigin natural product core. Tetrahedron, 76 (51). Art. No. 130755. ISSN 0040-4020. https://resolver.caltech.edu/CaltechAUTHORS:20191105-093732898

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Abstract

Derivitization of natural product scaffolds produces diversely functionalized molecules for biological study and offers insight into the reactivities of complex molecular architectures. In the present study, the tricyclic framework of the cyanthiwigin natural product family was employed as a platform for late-stage diversification. The design and synthesis of several non-natural “hybrid” molecules resembling both the cyanthiwigin and gagunin natural products was accomplished, and the results of these investigations are described herein.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1016/j.tet.2019.130755DOIArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2019 Elsevier Ltd. Received 21 September 2019, Revised 26 October 2019, Accepted 28 October 2019, Available online 1 November 2019. This work was supported by the NSF under the CCI Center for Selective C–H Functionalization (CCHF), CHE-1700982. Additional financial support was provided by Caltech and Novartis. Dr. David Horne and Dr. Sangkil Nam (City of Hope) are acknowledged for assistance with biological studies. Dr. David VanderVelde, Dr. Mona Shahgholi, and Naseem Torian are acknowledged for assistance with structural determination and characterization.
Funders:
Funding AgencyGrant Number
NSFCHE-1700982
CaltechUNSPECIFIED
NovartisUNSPECIFIED
Subject Keywords:Natural product hybrids; Late-stage diversification; Cyanthiwigins; Gagunins
Issue or Number:51
Record Number:CaltechAUTHORS:20191105-093732898
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20191105-093732898
Official Citation:Kelly E. Kim, Yuka Sakazaki, Brian M. Stoltz, Synthesis of non-natural cyanthiwigin–gagunin hybrids through late-stage diversification of the cyanthiwigin natural product core, Tetrahedron, Volume 76, Issue 51, 2020, 130755, ISSN 0040-4020, https://doi.org/10.1016/j.tet.2019.130755.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:99664
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:05 Nov 2019 17:45
Last Modified:21 Dec 2020 20:47

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