Indole-Diterpene Synthetic Studies: Total Synthesis of (−)-21-Isopentenylpaxilline

✍ Scribed by Amos B. Smith III; Haifeng Cui

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 522 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390328

✦ Synopsis

Abstract

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.