The paper presents approaches to the synthesis of ether derivatives of the antiparkinsonian agent Prottremine ((1,2,6)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol) at positions 1 and 9. The synthesis of the 1-methoxy derivative was carried out by isomerization of verbenol epoxide methyl ether on K10 montmorillonite clay with a yield of 31%. The synthesis of 9-MeO-, 9--PrO- and 9--BuO-derivatives was developed on the basis of the 9-Br-derivative by sequential introduction of methoxymethyl protection, interaction with the corresponding alcoholates and removal of the protecting groups. The yield of the target compounds in three steps was 40–59%.
O.V. Ardashov (Thu,) studied this question.