Terpenes in organic synthesis 13. Synthesis of s-(+)-methoprene from (+)-β-citronellene
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S-(+)-Methoprene (I) was synthesized from (+)-β-citronellene (III) with an optical purity of about 50%. The optical purity of the key intermediate, S-(−)-7-methoxy-3,7-dimethyl-1-octanol (IV), can be increased by fractional crystallization of the optically active acid phthalate salt (VI) followed by hydrolytic regeneration of alcohol (IV). The yield of (I) at the final synthetic stage can be increased by use of interphase catalysis. S-(+)-Methoprene has a higher morphogenetic activity than the racemic form.
KeywordsAlcohol Crystallization Catalysis Phthalate Terpene
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