Highly Stereocontrolled Synyhesis of Some Trioxygenated Cyclohexenes: An Asymmetric Total Synthesis of (-)-Methyl Triacetyl-4-epishikimate

Article abstract of DOI:10.1021/ja00283a036

Polyfunctional bicyclic lactone (-)-1 serves as a chiron for preparation of 3,4,6-trioxygenated cyclohexene (-)-5a in 56.6percent overall yield and for synthesis of (-)-methyl triacetyl-4-epishikimate, (-)-12, in 14 steps and in 23.4percent overall yield.