Ring-fused cyclobutanesviacycloisomerization of alkylidenecyclopropane acylsilanes

Author:

Eichenberger Sarah1234ORCID,Hönig Moritz1234ORCID,Richter Matthieu J. R.1234ORCID,Gershoni-Poranne Renana1234ORCID,Carreira Erick M.1234ORCID

Affiliation:

1. Laboratorium für Organische Chemie

2. Eidgenössische Technische Hochschule Zürich, HCI H335

3. 8093 Zürich

4. Switzerland

Abstract

A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed that involves tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes.

Funder

Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Reference52 articles.

1. Sesquiterpenes from Omphalotus illudens

2. Synthesis of Protoilludanes and Related Sesquiterpenes

3. Bicyclo[3.2.0]heptane as a Core Structure for Conformational Locking of 1,3-Bis-Pharmacophores, Exemplified by GABA

4. For reviews on the synthesis of cyclobutanes, see: E.Lee-Ruff , Synthesis of Cyclobutanes , in PATAI's Chemistry of Functional Groups , ed. Z. Rappoport , John Wiley & Sons, Ltd. , 2009

5. Total synthesis of -illudol

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