119245-18-0Relevant academic research and scientific papers
Ring Expansions of Photoadducts. Potential Applications in the Synthesis of Triquinane and Taxane Skeletons
Lange, Gordon L.,Decicco, Carl P.,Willson, Jennifer,Strickland, Lou Anne
, p. 1805 - 1810 (2007/10/02)
Photoadditions of enones 4 or 18 with cyclopentene gave in good yield adducts 5/6 or 20/21, respectively, with the anti isomers predominating by a ratio of ca. 9:1.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 products 12 or 28 as well as bridged products 13-14 or 29-32, respectively.The sequence starting with the enone 18 has potentialapplications in the synthesis of the triquinane and the taxol carbon skeletons.
