Tetrahedron

Photolysis of α-diazocyclopentanones. Ring contraction to functionalised cyclobutanes and synthesis of junionone, grandisol and planococcyl acetate

A Ghosh, UK Banerjee, RV Venkateswaran

Index: Gosh, Arun; Banerjee, Ujjal K.; Venkateswaran, R.V. Tetrahedron, 1990 , vol. 46, # 8 p. 3077 - 3088

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Citation Number: 11

Abstract

Photolysis of diazoketone 19 in methanol furnished the cyclobutane carboxylate 20. Photolysis in aqueous sodium bicarbonate-THF afforded the acid 21 in better yield. Reduction of the ester followed by oxidation and a subsequent Wittig reaction furnished±junionone (3). Photolysis of the diazoketone 24 resulted in a 1: 1 mixture of cyclobutane carboxylates 25. Treatment of the corresponding carboxylic acids with ...