Synthesis of spiro-annulated cyclobutane derivatives through ketene [2+2] cycloaddition and ring-rearrangement metathesis

Kotha, Sambasivarao ; Pulletikurti, Sunil

Abstract

Herein is reported a concise synthesis of spiro-annulated cyclobutane tetracyclic and pentacyclic derivatives by ketene addition, and ring-rearrangement metathesis (RRM) as key steps, starting with commercially available norbornadiene and dicyclopentadiene. The tetracyclic spiro-derivative contains a [5/5/4] core unit, which is the key building block to angular triquinanes synthesis. Whereas, the pentacyclic spiro-derivative contains a basic core skeleton of presilphiperfolanes, and other sesquiterpenoids.


Keyword(s)

Cyclobutane, spirocyclic, ketene addition, metathesis, dechlorination


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