Cycloaldol approach to the isobenzofuran core of eunicellin diterpenes
by Chai, Yonghai; Vicic, David A.; McIntosh, Matt C.
[GRAPHICS] A novel cycloaldol approach to the isobenzofuran core common to many of the eunicellin diterpenes is described. The cycloaldol precursor was prepared by aldol addition of (S)-(+)-carvone and methacrolein followed by etherification to a glycolate ester. Chemoselective enolization of the glycolate ester led to the cycloaldol adduct in high yield and diastereoselectivity. An oxidative rearrangement-allylic diazene rearrangement sequence established the requisite cis ring fusion.
- Organic Letters
- Start Page
- 1523-7052; 1523-7060