TY - JOUR ID - pittir20619 UR - http://d-scholarship-dev.library.pitt.edu/20619/ IS - 7 A1 - Haney, BP A1 - Curran, DP Y1 - 2000/04/07/ N2 - The synthesis and 'round trip radical cyclization' of 11-iodo-2,7,11- trimethyldodec-6-en-5-one are described. The round trip cyclization is a sequence of 5-exo, 6-endo, and 5-exo cyclizations in which the last radical cyclization occurs at the same carbon atom as the initial radical generation. The key second (6-endo) cyclization produces two stereoisomers, one of which cyclizes efficiently to isogymnomitrene ketone, while the other cyclizes inefficiently to gymnomitrene ketone. Efforts to influence the kinetic or thermodynamic outcome of the second cyclization were not successful, and the results are contrasted with a related cyclization of Jung and Rayle where thermodynamic control was readily established. JF - Journal of Organic Chemistry VL - 65 SN - 0022-3263 TI - Round trip radical reactions from acyclic precursors to tricyclo[5.3.1.02,6]undecanes. A new cascade radical cyclization approach to (±)-isogymnomitrene and (±)-gymnomitrene SP - 2007 AV - public EP - 2013 ER -