TOTAL SYNTHESIS OF (+-)-PATCHOULI ALCOHOL AND (+-)-SEYCHELLENE VIA A COMMON HOMOISOTWISTANE INTERMEDIATE

被引:43
作者
YAMADA, K
KYOTANI, Y
MANABE, S
SUZUKI, M
机构
[1] Department of Chemistry, Faculty of Science, Nagoya University, Chikusa, Nagoya
关键词
D O I
10.1016/0040-4020(79)80064-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Base-catalyzed cyclization of a conjugated cyclohexenone derivative 16 afforded in a single step a homoisotwistane derivative 17, which was converted to a ketone 22. Both (±)-patchouli alcohol 1 and (±)-seychellene 2 were synthesized using reactions at the bridgehead position (C-7) of a bicyclo[3.3.1]nonan-2-one system contained in 22. © 1979.
引用
收藏
页码:293 / 298
页数:6
相关论文
共 37 条
[1]   TERPENES .14. SYNTHESIS OF PATCHOULI ALCOHOL [J].
BUCHI, G ;
MACLEOD, WD ;
PADILLA, JO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (20) :4438-&
[2]  
BURGER U, 1970, TETRAHEDRON LETT, P3057
[3]  
CHAKRAVARTI D, 1965, J INDIAN CHEM SOC, V42, P607
[4]  
COREY EJ, 1975, TETRAHEDRON LETT, P2647
[5]  
DANISHEFSKY S, 1968, J CHEM SOC CHEM COMM, P1287
[6]  
DOBLER M, 1963, P CHEM SOC LONDON, P383
[7]   SYNTHESIS OF (+/-) SEYCHELLENE [J].
FRATER, G .
HELVETICA CHIMICA ACTA, 1974, 57 (01) :172-179
[8]   CARBENOID SPECIES FROM METHYL AND METHYLENE HALIDES [J].
FRIEDMAN, L ;
HONOUR, RJ ;
BERGER, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (15) :4640-&
[9]   DEHYDROBROMINATION OF "3-BROMOTRICYCLO[5.3.1.03,8]UNDECANE (3-BROMO-4-HOMOISOTWISTANE) AND SOME ADDITION-REACTIONS OF TRICYCLO[5.3.1.03,8]-UNDEC-2-ENE - STEREOCHEMISTRY OF FORMATION AND REACTION OF AN ANTI-BREDT COMPOUND PROBED BY DEUTERIUM SUBSTITUTION [J].
FUJIKURA, Y ;
INAMOTO, Y ;
TAKAISHI, N ;
IKEDA, H ;
AIGAMI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (20) :2133-2137
[10]   TOTAL SYNTHESIS OF (+/-)-SEYCHELLENE [J].
FUKAMIYA, N ;
KATO, M ;
YOSHIKOSHI, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (17) :1843-1847