Linear Tetraquinanes by Microwave Assisted [3+2] Cycloaddition and Ring‐Rearrangement Metathesis

Abstract

AbstractHerein, an improved synthetic strategy to linear tetraquinanes is reported via a [3+2] cycloaddition and ring‐rearrangement metathesis as key steps. The linear tetraquinanes reported earlier were synthesized in a nine step sequence with an overall yield of 9 % while the same tetraquinanes are now prepared in four steps with a 3‐fold increase in overall yield of 29 %. Failure of the conventional [3+2] cycloaddition using allyltriisopropylsilane was overcome by using microwave irradiation (MWI) conditions which is performed for the first time for this purpose. The strategy reported here does not involve any protection and deprotection steps and can be helpful for the synthesis of polyquinane based natural products and synthesis of medicinally important targets.