Rapid assembly of the bicyclo[5.3.1]undecenone core of penostatin F: a successive Diels-Alder/Claisen reaction strategy with an efficient stereochemical relay.

Abstract

The first synthesis of the tricyclic core of Penostatin F (1) using a stereocontrolled Diels-Alder reaction and a Claisen rearrangement in succession has been achieved in nine steps from commercially available methyl acetoacetate and (E)-2-decenal. Penostatin F is a metabolite isolated from a fungal strain of Penicillium sp., OUPS-79, separated from the marine alga Enteromorphia intestinalis and exhibits significant cytotoxicity against cultured P388 Leukemia cells (ED(50) = 1.4 micromol/mL). [reaction: see text]

• Authors: Louis Barriault, Patrick J A Ang, Roch M A Lavigne
• Journal: Organic letters (Org Lett) Vol. 6 Issue 8 Pg. 1317-9 (Apr 15 2004) ISSN: 1523-7060 [Print] United States
• PMID: 15070326 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 4,5-epoxy-2-decenal
• Acetoacetates
• Aldehydes
• Benzopyrans
• Bridged Bicyclo Compounds, Heterocyclic
• Epoxy Compounds
• penostatin F

Topics

• Acetoacetates (chemistry)
• Aldehydes (chemistry)
• Animals
• Benzopyrans (chemical synthesis, pharmacology)
• Bridged Bicyclo Compounds, Heterocyclic (chemical synthesis, pharmacology)
• Cyclization
• Epoxy Compounds (chemistry)
• Molecular Structure
• Stereoisomerism