An approach to the synthesis of the eupomatilones

by Hong, Sang Phyo; McIntosh, Matt C.

[GRAPHICS] 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.

Journal
Organic Letters
Volume
4
Issue
1
Year
2002
Start Page
19
ISBN/ISSN
1523-7052; 1523-7060
DOI
10.1021/ol0167816