72 ジテルペン系フェノール誘導体のオゾン酸化 : 光学活性ドリマン型セスキテルペン類及びフラノセスキテルペンの合成

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Ozonolysis of phenolic dehydroabietic acid derivatives was investigated and products obtained by the cleavage of the aromatic ring by means of ozonolysis was found to be governed by the substitution pattern of the hydroxyl group in the aromatic ring. I) Ozonolysis of the 12-hydroxy compound (8) gave the pentanor-labdane type compounds (36), (37), and (38), the cleavage being taken place at the dotted line a. II) Ozonolysis of the 11,12-hydroxy compound (10), 14-hydroxy compound (24), and 13,14-dihydroxy compound (34) afford the drimane type compounds. In these case, the cleavage took place at the dotted line b. By use of the above method, we succeeded in the syntheses of the optically active (+)-isodrimenin (39), (+)-confertifolin (41), (+)-valdiviolide (42), and (+)-winterin (43). Then ozonolysis of the 6-substituted-14-hydroxy compounds (60) and (61) gave the 6-substituted confertifolin derivatives (58) and (59) which were converted into the optically active (+)-fragrolide (55) and (+)-bemadienolide (56). III) Ozonolysis of the 13-hydroxy compound (28) gave the pallescensins A type compound (49), the cleavage being taken place at the dotted line c. 49 was successfully converted into the optically active (+)-pallescensins A (50). In addition, we report the short syntheses of (+)-confertifolin (41) and (+)-isodrimenin (39) from β-ionone (75).
天然有機化合物討論会の論文
1978-08-22