Collect. Czech. Chem. Commun. 1989, 54, 3284-3293

The hydroalumination-iodination of enyne α-alcohols: Synthesis of 3-methyl-2,4-alkadien-1-ols

Ashot P. Khrimyana, Oganes A. Gharibyana, Ludvík Streinzb, Zdeněk Wimmerb, Miroslav Romaňukb and Shaliko O. Badanyana

a Institute of Organic Chemistry, Armenian Academy of Sciences, 375 094 Yerevan, U.S.S.R.
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia


It has been found that the reaction course of hydroalumination-iodination using 2-methyl-5-hexen-3yn-2-ol and (6E)-9,13-dimethyl-6,12-tetradecadien-4-yn-3-ol as substrates is ambiguous. The subsequent reaction of lithium dimethyl cuprate with iodo dienols unlike that of iodo alkenols is non-stereoselective. These reactions have been used for the synthesis of a juvenile hormone mimic (4E, 6E)-5,9,13-trimethyl-4,6,12-tetradecatrien-3-ol.