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Indole‐Diterpene Synthetic Studies: Total Synthesis of (−)‐21‐Isopentenylpaxilline
Author(s) -
Smith Amos B.,
Cui Haifeng
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390328
Subject(s) - chemistry , diterpene , total synthesis , indole test , stereochemistry , organic chemistry , combinatorial chemistry
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.