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Late-Stage Diversification: A Motivating Force in Organic Synthesis

Kim, Kelly E. and Kim, Alexia N. and McCormick, Carter J. and Stoltz, Brian M. (2021) Late-Stage Diversification: A Motivating Force in Organic Synthesis. Journal of the American Chemical Society, 143 (41). pp. 16890-16901. ISSN 0002-7863. doi:10.1021/jacs.1c08920. https://resolver.caltech.edu/CaltechAUTHORS:20211012-211826965

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Abstract

Interest in therapeutic discovery typically drives the preparation of natural product analogs, but these undertakings contribute significant advances for synthetic chemistry as well. The need for a highly efficient and scalable synthetic route to a complex molecular scaffold for diversification frequently inspires new methodological development or unique application of existing methods on structurally intricate systems. Additionally, synthetic planning with an aim toward late-stage diversification can provide access to otherwise unavailable compounds or facilitate preparation of complex molecules with diverse patterns of substitution around a shared carbon framework. For these reasons among others, programs dedicated to the diversification of natural product frameworks and other complex molecular scaffolds have been increasing in popularity, a trend likely to continue given their fruitfulness and breadth of impact. In this Perspective, we discuss our experience using late-stage diversification as a guiding principle for the synthesis of natural product analogs and reflect on the impact such efforts have on the future of complex molecule synthesis.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.1c08920DOIArticle
ORCID:
AuthorORCID
Kim, Kelly E.0000-0002-4132-2474
Kim, Alexia N.0000-0002-4060-8892
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2021 American Chemical Society. Received: August 23, 2021; Published: October 6, 2021. We acknowledge the NSF under the CCI Center for Selective C–H Functionalization (CCHF), CHE-1700982, NIH-NIGMS (R01GM127972A and R01GM080269), Caltech, and the University of Washington Tacoma for funding and support. We also thank current and former co-workers for helpful discussions and feedback on the preparation of this manuscript. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NSFCHE-1700982
NIHR01GM127972A
NIHR01GM080269
CaltechUNSPECIFIED
University of Washington TacomaUNSPECIFIED
Subject Keywords:Scaffolds, Molecules, Oxidation, Hydrogenation, Pharmaceuticals
Issue or Number:41
DOI:10.1021/jacs.1c08920
Record Number:CaltechAUTHORS:20211012-211826965
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20211012-211826965
Official Citation:Late-Stage Diversification: A Motivating Force in Organic Synthesis. Kelly E. Kim, Alexia N. Kim, Carter J. McCormick, and Brian M. Stoltz. Journal of the American Chemical Society 2021 143 (41), 16890-16901; DOI: 10.1021/jacs.1c08920
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:111369
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:14 Oct 2021 14:36
Last Modified:09 Nov 2021 00:02

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