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Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

Holman, K. R. and Stanko, A. M. and Reisman, S. E. (2021) Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis. Chemical Society Reviews, 50 (14). pp. 7891-7908. ISSN 0306-0012. https://resolver.caltech.edu/CaltechAUTHORS:20210527-093457647

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Abstract

Palladium-catalyzed cascade cyclizations (PCCs) are powerful synthetic tools that enable rapid assembly of polycyclic scaffolds. Palladium complexes can promote a variety of carbon–carbon and carbon–heteroatom bond-forming reactions with high chemo-, enantio-, and diastereoselectivity. The combination of multiple ring-forming elementary steps into a single cascade sequence can allow complex structures to be accessed with high step economy. This strategy has been employed to access natural products in several distinct classes, including the mitomycins, dragmacidins, isoryanodane diterpenes, and ergot alkaloids. In this tutorial review, we demonstrate how PCCs have expedited natural product synthesis by enabling the formation of both C–C and C–X (X = O, N) bonds in a single synthetic operation.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/d0cs01385dDOIArticle
ORCID:
AuthorORCID
Holman, K. R.0000-0001-6424-9479
Stanko, A. M.0000-0003-0576-3739
Reisman, S. E.0000-0001-8244-9300
Additional Information:© The Royal Society of Chemistry 2021. Submitted 15 Feb 2021; First published 26 May 2021. We thank colleagues Travis DeLano, Sara Dibrell, and Michael Maser (all of Caltech) for providing insightful feedback during the writing process. K. R. H. was supported by a National Defense Science and Engineering Graduate Fellowship. S. E. R. is a Heritage Medical Research Institute Investigator, and acknowledges financial support from the NSF (CHE-1800536). There are no conflicts to declare.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
Heritage Medical Research InstituteUNSPECIFIED
NSFCHE-1800536
Issue or Number:14
Record Number:CaltechAUTHORS:20210527-093457647
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210527-093457647
Official Citation:Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis. Chem. Soc. Rev., 2021, 50, 7891-7908; DOI: 10.1039/d0cs01385d
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:109280
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:27 May 2021 17:24
Last Modified:26 Jul 2021 18:07

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