%0 Journal Article %A Roberson, Claudia W. %A Woerpel, K. A. %D 2000 %T Formal Synthesis of (±)-Peduncularine:  Use of the [3 + 2] Annulation of Allylic Silanes and Chlorosulfonyl Isocyanate %U https://acs.figshare.com/articles/journal_contribution/Formal_Synthesis_of_-Peduncularine_Use_of_the_3_2_Annulation_of_Allylic_Silanes_and_Chlorosulfonyl_Isocyanate/3761739 %R 10.1021/ol9913744.s001 %2 https://acs.figshare.com/ndownloader/files/5869050 %K annulation %K alkaloid %K Annulation %K allylic %K Formal Synthesis %K bicyclic lactam 7 %K Allylic Silanes %K Peduncularine %K conversion %K cyclohexadienyl silane 6 %K chlorosulfonyl isocyanate %K peduncularine %K Chlorosulfonyl Isocyanate %K synthesis %X The formal synthesis of the alkaloid (±)-peduncularine (1) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane 6 with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam 7. Conversion of this intermediate to 2 in three steps completed the formal synthesis of (±)-peduncularine. %I ACS Publications