SYNTHETIC STUDIES OF SESQUITERPENES WITH A CIS-FUSED DECALIN SYSTEM .6. ISOLATION, STRUCTURE ELUCIDATION, AND SYNTHESIS OF NORSESQUIBENIHIOL AND THE SYNTHESIS OF DEHYDROCHAMAECYNENOL

被引:4
作者
ANDO, M [1 ]
KIKUCHI, K [1 ]
ISOGAI, K [1 ]
IBE, S [1 ]
ASAO, T [1 ]
机构
[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN
来源
JOURNAL OF NATURAL PRODUCTS-LLOYDIA | 1995年 / 58卷 / 02期
关键词
D O I
10.1021/np50116a003
中图分类号
Q94 [植物学];
学科分类号
071001 [植物学];
摘要
Norsesquibenihol, a new norsesquiterpene alcohol, was isolated from the essential oil of Chamaecyparis formosensis and its structure was elucidated as 8 by spectroscopic methods. Allylic rearrangement of the 3 beta- and 3 alpha-alcohols 18 and 19, which were derived from the known acetylenic ketone 9 in three steps, gave a mixture of 8 and dehydrochamaecynenol [6]. The structure of norsesquibenihiol [8] was therefore proved by this synthesis.
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页码:177 / 183
页数:7
相关论文
共 10 条
[1]
SYNTHETIC STUDIES OF SESQUITERPENES WITH A CIS-FUSED DECALIN SYSTEM .5. A SYNTHETIC APPROACH TO THE STUDY OF STRUCTURE-ACTIVITY-RELATIONSHIPS OF THE TERMITICIDAL NORSESQUITERPENOIDS, CHAMAECYNONE AND RELATED-COMPOUNDS [J].
ANDO, M ;
KIKUCHI, K ;
ISOGAI, K ;
ISHIWATARI, T ;
HIRATA, N ;
YAMAZAKI, H .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (07) :924-933
[2]
THE TOTAL SYNTHESES OF CHAMAECYNONE, ISOCHAMAECYNONE, AND DIHYDROISOCHAMAECYNONE [J].
ANDO, M ;
ASAO, T ;
HIRATSUKA, N ;
TAKASE, K ;
NOZOE, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (05) :1425-1434
[3]
ANDO M, 1969, TETRAHEDRON LETT, P4689
[4]
THE TOTAL SYNTHESIS OF HYDROXYISOCHAMAECYNONE AND ITS STEREOCHEMICAL ASSIGNMENT [J].
ANDO, M ;
ASAO, T ;
TAKASE, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) :1039-1044
[5]
ASAO T, 1968, TETRAHEDRON LETT, P3639
[6]
NOZOE T, 1966, TETRAHEDRON LETT, P3663
[7]
NOZOE T, 1967, TETRAHEDRON LETT, P2821
[8]
ROLE OF ESSENTIAL OIL IN RESISTANCE OF CONIFEROUS WOODS TO TERMITE ATTACK [J].
SAEKI, I ;
SUMIMOTO, M ;
KONDO, T .
HOLZFORSCHUNG, 1971, 25 (02) :57-&
[9]
TERMITICIDAL SUBSTANCES FROM WOOD OF CHAMAECYPARIS-PISIFERA DON,D [J].
SAEKI, I ;
SUMIMOTO, M ;
KONDO, T .
HOLZFORSCHUNG, 1973, 27 (03) :93-96
[10]
TAKASE K, 1968, CHEM IND-LONDON, P1638