24 光学活性エポキシドを目的とするかまたは中間体として用いる天然物合成

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Chiral epoxides are known among natural products as important biosynthetic intermediates or biologically active compounds. We undertook the studies on chiral epoxides with a special emphasis on their roles as intermediates in natural products syntheses. A) Chiral epoxides as targets. (+)-Disparlure (1) and its antipode (2), the pheromone of gypsy moth, was synthesized stereoselectively starting from L-(+)-tartaric acid (6). B) Chiral epoxides as precursors of lactones. The (S)-(+)-isomer (3) of massoilactone, a defense substance of formicine ants, was synthesized from D-(+)-glyceraldehyde acetonide (25). The same starting material was converted into the antipode (4) of (-)-pestalotin, the gibberellin synergist. C) Epoxides as precursors of alcohols. The stereochemistry of (-)-4-methylheptan-3-ol (43), a component of the pheromone complex of smaller European elm bark beetle, was established as (3S: 4S)-threo (68) by synthetic works including the preparation of its enantiomer (5) from (R)-(+)-citronellic acid (58).
天然有機化合物討論会の論文
1976-09-20