An approach to the synthesis of the eupomatilones.
[structure: see text] A concise approach to the eupomatilone family of lignans is presented. The strategy employs an intramolecularly competitive Ireland-Claisen rearrangement of a densely functionalized bis-allylic ester. The rearrangement serves both to construct the A-ring and to establish the stereochemistry at C(3) and C(4).
Hong
Sang-phyo
SP
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA.
McIntosh
Matthias C
MC
D001315:Australia; D007202:Indicators and Reagents; D017705:Lignans / Q000138:chemical synthesis*; D029562:Magnoliaceae; D008968:Molecular Conformation; D010944:Plants / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D017705:Lignans