Total synthesis of (+/-)-chartelline C |
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Authors: | Baran Phil S Shenvi Ryan A |
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Affiliation: | Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, CA 92037, USA. |
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Abstract: | 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 beta-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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