4.6 Article

Rapid construction of cyclopenta[b]naphthalene frameworks from propargylic alcohol tethered methylenecyclopropanes

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 37, Pages 7396-7400

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob01732a

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Funding

  1. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  2. National Natural Science Foundation of China [21372250, 21121062, 21302203, 20732008, 21772037, 21772226, 21861132014, 91956115]
  3. Fundamental Research Funds for the Central Universities [222201717003]

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We have developed a new synthetic methodology for the rapid construction of cyclopenta[b]naphthalene frameworks from the reaction of propargylic alcohol tethered methylenecyclopropanes with mesyl chloride in the presence of triethylamine through cascade cyclization. The reaction can be performed under mild conditions without the use of transition metals, affording the target products in moderate to good yields, and this cyclization reaction process can be scaled up to a gram-scale synthesis.

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