摘要：

An efficient, stereocontrolled total synthesis of the complex indole-diterpene alkaloid ()-21-isopentenylpaxilline ( 1 ) has been achieved. Key elements of the synthesis include the stereocontrolled construction of the advanced eastern hemisphere ()- 68 , involving a highly efficient union of the eastern and western fragments ()- 68 and 5 exploiting our 2-substituted indole synthesis, application of the Negishi π cycloalkylation tactic as a new, potentially general protocol for the construction of ring C, and the fragmentation of a β , γ -epoxy ketone to introduce the tertiary OH group at C(13) in the indole diterpene skeleton.

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