Total synthesis of (-)-21-isopentenylpaxilline.
[structure: see text] The total synthesis of (-)-21-isopentenylpaxilline (1) has been achieved. Key elements of the synthesis include the stereocontrolled construction of the advanced eastern hemisphere (-)-5, a highly efficient union of the eastern and western fragments (-)-5 and 4, respectively, exploiting our 2-substituted indole synthesis, and a new protocol for the construction of ring C.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Cui
Haifeng
H
D000470:Alkaloids / Q000138:chemical synthesis; D007211:Indoles / Q000138:chemical synthesis*; D007306:Insecticides / Q000138:chemical synthesis; D003904:Mitosporic Fungi / Q000737:chemistry*; D013237:Stereoisomerism
C475533:21-isopentenylpaxilline; D000470:Alkaloids; D007211:Indoles; D007306:Insecticides