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Issue 2, 2020
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Occurrence, synthesis and applications of natural and designed [3.3.3]propellanes

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Abstract

Covering: 1978 to 2019

The synthetically challenging [3.3.3]propellane core has caught a lot of attention over the last 50 years. This comprehensive review details all synthetic strategies reported in the period 1978–2019 to facilitate the synthesis of carbocyclic [3.3.3]propellanes. The described strategies span from acid-catalyzed rearrangements and photo-mediated cycloadditions of ketones, heteropropellanes and dispiroundecanes to thermal rearrangements of acetylenes and alkenes. Other approaches, such as radical reactions with halogenated alkenes, domino cyclizations, the smart use of epoxide-carbonyl rearrangements and intramolecular palladium-catalyzed ring contractions are discussed as well. A special section is dedicated to triptindanes, a subclass of [3.3.3]propellanes which are of interest to material sciences.

Graphical abstract: Occurrence, synthesis and applications of natural and designed [3.3.3]propellanes

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Article information


Submitted
10 Oct 2018
First published
29 May 2019

This article is Open Access

Nat. Prod. Rep., 2020,37, 224-245
Article type
Review Article

Occurrence, synthesis and applications of natural and designed [3.3.3]propellanes

A. M. Dilmaç, T. Wezeman, R. M. Bär and S. Bräse, Nat. Prod. Rep., 2020, 37, 224
DOI: 10.1039/C8NP00086G

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