Synthesis of the cyclic isomer of the vitamin K1 dihydro derivative (naphthotocopherol) and its analogs with the shortened and ω-functionalized side chain

Abstract

2RS,4´RS,8´RS) Naphthotocopherol and its optically active short chain analog were syn thesized by the condensation of menadiol acetate with (3RS,7RS,11RS) isophytol and (3RS,4S) 3,4,8 trimethylnon 1 en 3 ol (ee ~50%) in the presence of aluminosilicate Zeocar 10. Using (+) camphor 10 sulfonic acid as a catalyst, naphthotocopherol analogs with the unsaturated isoprenoid side chain were obtained from (3RS) linalool or (3RS,4S) 3,4,8 trimethylnona 1,7 dien 3 ol. Ozonolysis of these compounds produced the corresponding ω formyl derivatives.