A rapid stereocontrolled entry to the ABCD tetracyclic core of neotuberostemonine

Kevin I. Booker-Milburn*, Paul Hirst, Jonathan P H Charmant, Luke H J Taylor

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

26 Citations (Scopus)

Abstract

Four out of the five rings of the alkaloid neotuberostemonine (1) are present in the advanced precursor 2. The tetracyclic compound 2 has now been prepared in a short, linear route via lactone acid 3. A key step in the synthesis was the cuprate-mediated SN2′ ring-opening desymmetrization of the C2-symmetric bislactone 4.

Translated title of the contributionA Rapid Stereocontrolled Entry to the ABCD Tetracyclic Core of Neotuberostemonine
Original languageEnglish
Pages (from-to)1642-1644
Number of pages3
JournalAngewandte Chemie - International Edition
Volume42
Issue number14
DOIs
Publication statusPublished - 11 Apr 2003

Bibliographical note

Publisher: Wiley

Keywords

  • Asymmetric synthesis
  • Cuprates
  • Lactones
  • Natural products
  • Photocyclization
  • Total synthesis

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