180963-58-0Relevant academic research and scientific papers
Stereoselective Construction of Copaborneol and Longiborneol Frameworks by Intramolecular Double Michael Reaction
Ihara, Masataka,Makita, Kei,Fujiwara, Yuki,Tokunaga, Yuji,Facumoto, Keiichiro
, p. 6416 - 6421 (2007/10/03)
Stetreoselective synthesis of tricyclo3,8>decane 22 and tricyclo3,9>undecane 26 the basic skeleton of copaborneol and longiborneol, were achieved by the intramolecular double Michael reactions of 2-cyclopenten-1-ones 15-17.The substrates were prepared starting with tricyclo2,6>deca-4,8-dien-3-one (6).The intramolecular double Michael reactions were carried out under three different conditions: TMSCl-Et3N-ZnCl2.TMSI-(TMS)2NH, and Bu2BOTf-(TMS)2NH.The framework 26 of longiborneol was constructed in good yield using the latter two reagent systems.
