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Synthesis 2018; 50(22): 4359-4368
DOI: 10.1055/s-0037-1610437
DOI: 10.1055/s-0037-1610437
paper
Short Enantioselective Formal Synthesis of (–)-Platencin
We thank the NIH-NIGMS (R01 GM080269), DAAD (postdoctoral fellowship to C.D.), Eli Lilly (predoctoral fellowship to J.T.M.), Amgen, Bristol-Myers Squibb, Merck Research Laboratories, Abbott Laboratories, Boehringer-Ingelheim, and Caltech for generous funding. We also thank the UIC Department of Chemistry (startup funds to J.T.M.) and the National Science Foundation (CAREER Award 1654490 to J.T.M.).Further Information
Publication History
Received: 03 May 2018
Accepted after revision: 29 May 2018
Publication Date:
23 July 2018 (online)
Dedicated to Prof. Dr. Scott E. Denmark on the occasion of his 65th birthday.
Abstract
A short enantioselective formal synthesis of the antibiotic natural product platencin is reported. Key steps in the synthesis include enantioselective decarboxylation alkylation, aldehyde/olefin radical cyclization, and regioselective aldol cyclization.
Key words
formal synthesis - palladium - enantioselective reactions - enantioconvergent synthesis - alkylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610437.
- Supporting Information
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References
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For syntheses of platencin, see:
For syntheses of platensimycin, see:
For recent reviews of allylic alkylation of ketone enolates, see:
For selected applications in total synthesis efforts in our group, see:
For accounts of the development of PHOX ligands, see:
We have developed an efficient multi-gram scale synthesis of PHOX ligands, see: