Literature DB >> 17061876

Total synthesis of (+/-)-chartelline C.

Phil S Baran1, Ryan A Shenvi.   

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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Year:  2006        PMID： 17061876     DOI： 10.1021/ja0659673

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

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4.  Studies towards the synthesis of the marine alkaloid chartelline C.

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8.  Chemoselectivity: the mother of invention in total synthesis.

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