4.7 Article

Construction of Cyclopenta[b]naphthalenol Frameworks by Weinreb Amide-Directed Umpolung Ring Opening of Methylenecyclopropanes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 22, Pages 3948-3953

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200991

Keywords

methylenecyclopropanes; cascade cyclization; weinreb amide; umpolung ring opening

Funding

  1. National Natural Science Foundation of China [21372250, 21121062, 21302203, 20732008, 21772037, 21772226, 21861132014, 91956115, 22171078]
  2. Fundamental Research Funds for the Central Universities [222201717003]

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A cascade cyclization method using Weinreb amide-tethered methylenecyclopropanes and alkynes is disclosed in this paper, which extends the umpolung ring opening of methylenecyclopropanes and provides a synthetic approach for constructing polycyclic cyclopenta[b]naphthalenol framework.
A cascade cyclization from Weinreb amide-tethered methylenecyclopropanes and alkynes has been disclosed in this paper, which extends the umpolung ring opening of methylenecyclopropanes, giving a synthetic approach for the construction of polycyclic cyclopenta[b]naphthalenol framework. In the protocol, four carbon-carbon bonds and two carbocycles are formed without the use of transition metals, providing a tool for constructing the structure-related polycyclic compounds.

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