Total Synthesis of (±)-Chartelline C

The first total synthesis of (±)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive β-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation.

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PID https://www.doi.org/10.1021/ja0659673.s004
PID https://www.doi.org/10.1021/ja0659673.s002
URL https://figshare.com/articles/Total_Synthesis_of_Chartelline_C/3050620
URL http://dx.doi.org/10.1021/ja0659673.s004
URL https://figshare.com/articles/dataset/Total_Synthesis_of_Chartelline_C/3050599
URL https://figshare.com/articles/Total_Synthesis_of_Chartelline_C/3050599
URL http://dx.doi.org/10.1021/ja0659673.s002
URL https://figshare.com/articles/dataset/Total_Synthesis_of_Chartelline_C/3050620
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Access Right Open Access
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Author Baran, Phil S.
Author Shenvi, Ryan A.
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Collected From figshare
Hosted By figshare
Publication Date 2016-02-29
Publisher Figshare
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Language UNKNOWN
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Source https://science-innovation-policy.openaire.eu/search/dataset?datasetId=dedup_wf_001::c4ad5e683db964163b3b07d36b7103ad
Author jsonws_user
Last Updated 15 December 2020, 18:27 (CET)
Created 15 December 2020, 18:27 (CET)