Development of the [3 + 2] annulations of cyclohexenylsilanes and chlorosulfonyl isocyanate: application to the total synthesis of (+/-)-peduncularine.
The synthesis of (+/-)-peduncularine was accomplished using the [3 + 2] annulation of an allylic silane with chlorosulfonyl isocyanate to assemble the bicyclic core of the alkaloid. The stereochemistry of the annulation product was employed to control the installation of the indolylmethyl side chain at C-7 with complete stereoselectivity.
Roberson
Claudia W
CW
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
D000470:Alkaloids / Q000138:chemical synthesis*; D003510:Cyclohexanes / Q000737:chemistry*; D053138:Cyclohexenes; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis*; D017953:Isocyanates / Q000737:chemistry*; D010944:Plants / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D003510:Cyclohexanes; D053138:Cyclohexenes; D026121:Indole Alkaloids; D007211:Indoles; D017953:Isocyanates; D012821:Silanes; C467792:peduncularine; C052568:cyclohexene