28 摂食阻止物質(±)-Warburgana/およびその関連化合物の全合成

概要

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Warburganal (1), isolated from the bark of Warburgia (Canellaceae)(W. stuhlmannii and W. ugandensis), is an extremely effective antifeedant against the African army worms. In addition, it exhibits a number of other activities such as antibiotics, molluscicidal and cytotoxicity (KB test, 0.01μg/ml). We have studied the total syntheses of (+)-warburganal and related compounds. 1) Syntheses of isodrimenin (9) and confertifolin (10) 1-A) (+)-Isodrimenin (9) and (+)-confertifolin (10) have already been synthesized from dehydroabietic acid (6) by the ozonolysis of its phenolic derivatives in our laboratory. 1-B) A large-scale preparation of (+)-(9) and (+)-(10) from β-Ionone (11) has been developed. 2) Synthesis of (+)-warburganal (1) (+)-Isodrimenin (9) was converted into the diol (39) via the triol (31) in eight steps. Moffatt oxidation of 39 gave the α-hydroxy aldehyde (43) in 73% yield, which was hydrolyzed to give (+)-warburganal (1). 3) Synthesis of (+)-cinnamosmolide (5) 4) Synthesis of (+)-cinnamodial (2) (+)-Cinnamosmolide (5) and (+)-cinnamodial (2) were synthesized from the common intermediate (36).
天然有機化合物討論会の論文
1979-09-20