Total synthesis of aquatolide

Open Access
Authors
Publication date 2015
Journal Organic Letters
Volume | Issue number 17 | 15
Pages (from-to) 3892-3894
Organisations
  • Faculty of Science (FNWI) - Van 't Hoff Institute for Molecular Sciences (HIMS)
Abstract A total synthesis of the sesquiterpene lactone aquatolide has been accomplished. The central step is an intramolecular [2 + 2]-photocycloaddition of an allene onto an alpha,beta-unsaturated delta-lactone. Other key steps are an intramolecular Horner-Wadsworth-Emmons reaction to close the lactone and an intramolecular Mukaiyama-type aldol reaction to cyclize the eight-membered ring. Racemic aquatolide has been resolved using preparative HPLC.
Document type Article
Note With supporting information
Language English
Published at
Downloads
500483 (Final published version)
Supplementary materials
Permalink to this page
Back