Preparation and absolute configuration of (-)-(E)-α-trans-bergamotenone

被引：17
|
作者：
Chapuis, C [1 ]
Barthe, M [1 ]
Muller, BL [1 ]
Schulte-Elte, KH [1 ]
机构：
[1] Firmenich SA, Corp R&D Div, CH-1211 Geneva 8, Switzerland
来源：
HELVETICA CHIMICA ACTA | 1998年 / 81卷 / 01期
关键词：
D O I：
10.1002/hlca.19980810114
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis, absolute configuration, and olfactive evaluation of (-)-(E)-alpha-trans-bergamotenone (=(-)-(1'S,6'R,E)-5-(2',6'-dimethylbicyclo[3.1.1]hept-2'-en-6'-yl)pent-3-en-2-one; (-)-1), as well as its homologue (-)-19 are reported. The previously arbitrarily attributed absolute configuration of 1 and of (-)-alpha-trans-bergamotene (=(-)-(1S,6R)-2,6-dimethyl-6-(4-methylpent-3-enyl)bicyclo[3.1.1]hept-2-ene; (-)-2), together with those of the structurally related aldehydes (-)-3a,b and alcohols (-)-4a,b, have been rigorously assigned.
引用
收藏
页码：153 / 162
页数：10
相关论文
共 50 条
  • [1] Preparation and Absolute Configuration of (-)-(E)-a-trans-Bergamotenone
    Chapuis, C.
    Barthe, M.
    Muller, B. L.
    Schulte-Elte, K. H.
    Helvetica Chimica Acta, 81 (01):
  • [2] PREPARATION AND ABSOLUTE-CONFIGURATION OF TRANS-2-AMINOCYCLOPENTANOL ENANTIOMERS
    BARR, AA
    FRENCEL, I
    ROBINSON, JB
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (24): : 4180 - 4183
  • [3] Absolute Configuration of trans-Perhydroazulene
    Saito, Fumito
    Gerbig, Dennis
    Becker, Jonathan
    Schreiner, Peter R.
    ORGANIC LETTERS, 2020, 22 (10) : 3895 - 3899
  • [4] ABSOLUTE CONFIGURATION OF TRANS-CYCLOOCTENE
    COPE, AC
    MEHTA, AS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (06) : 1268 - &
  • [5] CONFORMATION AND ABSOLUTE CONFIGURATION OF (-)-TRANS-CYCLOOCTENE
    MANOR, PC
    PARKES, AS
    SHOEMAKE.DP
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (17) : 5260 - &
  • [6] PREPARATION, PROPERTIES AND ABSOLUTE CONFIGURATION OF (-))-ALLANTOIN
    SGRAVENM.EJ
    VOGELS, GD
    VANPELT, C
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, 1969, 88 (09): : 929 - &
  • [7] ABSOLUTE CONFIGURATION OF TRANS-2,6-DIMETHYLPIPERDINE
    HILL, RK
    MORGAN, JW
    JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (10): : 3451 - &
  • [8] THE ABSOLUTE-CONFIGURATION OF (-)-BETA-TRANS-BERGAMOTENE
    CANE, DE
    MCILWAINE, DB
    OLIVER, JS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 55 - ORGN
  • [9] ABSOLUTE-CONFIGURATION OF (-)-BETA-TRANS-BERGAMOTENE
    CANE, DE
    MCILWAINE, DB
    OLIVER, JS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) : 1285 - 1286
  • [10] ABSOLUTE CONFIGURATION OF TRANS-1,2-DIPHENYLCYCLOPROPANE
    TOMOSKOZI, I
    CHEMISTRY & INDUSTRY, 1965, (16) : 689 - +
12345