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Review
. 2023 Apr 21;88(8):4925-4941.
doi: 10.1021/acs.joc.2c02746. Epub 2023 Jan 27.

Palladium-Catalyzed Carbonylations: Application in Complex Natural Product Total Synthesis and Recent Developments

Hunter S Sims  1   2 , Mingji Dai  1
Affiliations
Review

Palladium-Catalyzed Carbonylations: Application in Complex Natural Product Total Synthesis and Recent Developments

Hunter S Sims et al. J Org Chem. .

Abstract

Carbon monoxide is a cheap and abundant C1 building block that can be readily incorporated into organic molecules to rapidly build structural complexity. In this Perspective, we outline several recent (since 2015) examples of palladium-catalyzed carbonylations in streamlining complex natural product total synthesis and highlight the strategic importance of these carbonylation reactions in the corresponding synthesis. The selected examples include spinosyn A, callyspongiolide, perseanol, schizozygane alkaloids, cephanolides, and bisdehydroneostemoninine and related stemona alkaloids. We also provide our perspective about the recent advancements and future developments of palladium-catalyzed carbonylations.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Total synthesis of spinosyn A (Dai, 2016).
Figure 2
Figure 2
Total synthesis of callyspongiolide (Harran, 2018).
Figure 3
Figure 3
Total synthesis of perseanol (Reisman, 2019).
Figure 4
Figure 4
Total syntheses of schizozygane alkaloids (Zhang, 2021).
Figure 5
Figure 5
Total syntheses of cephanolides B and C (Zhao, 2018).
Figure 6
Figure 6
Total syntheses of stemona alkaloids (Dai, 2018, 2020).
Figure 7
Figure 7
Recent examples of first-row transition metal carbonylative transformations.
Figure 8
Figure 8
Examples of photocatalytic carbonylative transformations.
Figure 9
Figure 9
Gaunt C–H carbonylation to β-lactams.
Figure 10
Figure 10
Recent example of photochemical carbonylation in flow.
Figure 11
Figure 11
Examples of recent enantioselective carbonylations.
Figure 12
Figure 12
Notable [11C] incorporation via palladium-mediated carbonylation.
Figure 13
Figure 13
Building structural complexity through palladium-catalyzed carbonylations.
See this image and copyright information in PMC

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