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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.).Weitere Informationen
Publikationsverlauf
Received: 03. Mai 2018
Accepted after revision: 29. Mai 2018
Publikationsdatum:
23. Juli 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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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: