- Synthesis of the cyclic isomer of the vitamin K1 dihydro derivative (naphthotocopherol) and its analogs with the shortened and ω-functionalized side chain
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(2RS,4′ RS,8′ RS)-Naphthotocopherol and its optically active short-chain analog were synthesized by the condensation of menadiol acetate with (3 RS,7 RS,11 RS)-isophytol and (3 RS,4 S)-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 (3 RS)-linalool or (3 RS,4 S)-3,4,8-trimethylnona-1,7-dien-3-ol. Ozonolysis of these compounds produced the corresponding ω-formyl derivatives.
- Spivak,Knyshenko,Mallyabaeva,Odinokov
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