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Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes.

ABSTRACT: A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed. The readily available starting materials participate in tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes, which are common motifs in terpenoid natural products. Notably, the transformation relies on the ability of acylsilanes to act sequentially as acceptors and donors on the same carbon atom.

SUBMITTER: Eichenberger S

PROVIDER: S-EPMC8159344 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Ring-fused cyclobutanes <i>via</i> cycloisomerization of alkylidenecyclopropane acylsilanes.

Eichenberger Sarah S Hönig Moritz M Richter Matthieu J R MJR Gershoni-Poranne Renana R Carreira Erick M EM

Chemical science 20200504 20

A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed. The readily available starting materials participate in tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes, which are common motifs in terpenoid natural products. Notably, the transformation relies on the ability of acylsilanes to act sequentially as acceptors and donors on the same carbon atom. ...[more]

PMID: 34122987

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