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

来源：

TETRAHEDRON | 1979年 / 35卷 / 03期

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

页码：293 / 298

页数：6

共 37 条

[1] TERPENES .14. SYNTHESIS OF PATCHOULI ALCOHOL
BUCHI, G
MACLEOD, WD
PADILLA, JO
[J]. 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
FRATER, G
[J]. HELVETICA CHIMICA ACTA, 1974, 57 (01) : 172 - 179
[8] CARBENOID SPECIES FROM METHYL AND METHYLENE HALIDES
FRIEDMAN, L
HONOUR, RJ
BERGER, JG
[J]. 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
FUJIKURA, Y
INAMOTO, Y
TAKAISHI, N
IKEDA, H
AIGAMI, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (20): : 2133 - 2137
[10] TOTAL SYNTHESIS OF (+/-)-SEYCHELLENE
FUKAMIYA, N
KATO, M
YOSHIKOSHI, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (17): : 1843 - 1847

← 1 2 3 4 →