Abstract
An efficient six-step synthesis of bicyclo[4.4.1]undecane-2,7-dione was elaborated. Key steps include an enantioselective oxazaborolidine-catalyzed borane reduction (CBS reduction) of 2,3,4,6,7,8-hexahydronaphthalene-1,5-dione to the corresponding diol, and a subsequent (syn-diastereoselective) cyclopropanation. Oxidation then gives tricyclo[4.4.1.01,6]undecane-2,7-dione (>99% ee) which on treatment with two equivalents of samarium(II) iodide undergoes cleavage of the central cyclopropane bond to yield the target compound without any loss of stereochemical information.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
