%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