Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis
- Creators
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Holman, K. R.
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Stanko, A. M.
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Reisman, S. E.
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.
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.Additional details
- Eprint ID
- 109280
- DOI
- 10.1039/d0cs01385d
- Resolver ID
- CaltechAUTHORS:20210527-093457647
- National Defense Science and Engineering Graduate (NDSEG) Fellowship
- Heritage Medical Research Institute
- CHE-1800536
- NSF
- Created
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2021-05-27Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute