Journal
HELVETICA CHIMICA ACTA
Volume 86, Issue 12, Pages 3908-3938Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.200390328
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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 pi cycloalkylation tactic as a new, potentially general protocol for the construction of ring C, and the fragmentation of a beta,gamma-epoxy ketone to introduce the tertiary OH group at C(13) in the indole diterpene skeleton.
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