Ring expansions of [2+ 2] photoadducts. Potential applications in the synthesis of triquinane and taxane skeletons

…, CP Decicco, J Willson, LA Strickland

Index: Lange, Gordon L.; Decicco, Carl P.; Willson, Jennifer; Strickland, Lou Anne Journal of Organic Chemistry, 1989 , vol. 54, # 8 p. 1805 - 1810

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Citation Number: 38

Abstract

Photoadditions of enones 4 or 18 with cyclopentene gave in good yield adducts 516 or 20121, respectively, with the anti isomers predominating by a ratio of-9: l. These adducts were converted to hydroxy ketones 9 or 24 by the following sequence: ketalization, LiAlH4 reduction, and hydrolysis. The alcohol function in these ketones was converted to a good leaving group, and the resultant derivatives were solvolyzed to give ring-expanded ...