Short synthetic route to the enantiomerically pure (R)-(+)-gamma-decalactone

被引:18
作者
Kula, J
Sikora, M
Sadowska, H
Piwowarski, J
机构
[1] Institute of General Food Chemistry, Technical University of Lodz
关键词
D O I
10.1016/0040-4020(96)00658-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient procedure for the preparation of homochiral (R)-(+)-gamma-decalactone 4 based on castor oil ozonolysis is described. The key intermediate, (R)-(-)-1,3-nonandiol 1, was transformed into monotosylate 1 and then reacted with sodium cyanide to give (R)-(-)-4-hydroxydecanitrile 3. Treatment of the latter with a dilute hydrochloric acid provided the enantiomerically pure lactone 4 Copyright (C) 1995 Elsevier Science Ltd
引用
收藏
页码:11321 / 11324
页数:4
相关论文
共 13 条
  • [1] Arctander S., 1969, Perfume and Flavor Chemicals (Aroma Chemicals), VI and II
  • [2] A SIMPLE ONE-POT SYNTHESIS OF NITRILES FROM ALCOHOLS
    CAMPS, F
    GASOL, V
    GUERRERO, A
    [J]. SYNTHETIC COMMUNICATIONS, 1988, 18 (04) : 445 - 452
  • [3] CHOUG JM, 1990, TETRAHEDRON LETT, V31, P1981
  • [4] CHIRALITY EVALUATION OF 1,4-DECANOLIDE IN PEACH
    FEUERBACH, M
    FROHLICH, O
    SCHREIER, P
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1988, 36 (06) : 1236 - 1237
  • [5] CHEMISTRY OF FRUIT-FLIES - COMPOSITION OF THE RECTAL GLAND SECRETION OF (MALE) DACUS-CUCUMIS (CUCUMBER FLY) AND DACUS-HALFORDIAE - CHARACTERIZATION OF (Z,Z)-2,8-DIMETHYL-1,7-DIOXASPIRO[5.5]UNDECANE
    KITCHING, W
    LEWIS, JA
    PERKINS, MV
    DREW, R
    MOORE, CJ
    SCHURIG, V
    KONIG, WA
    FRANCKE, W
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) : 3893 - 3902
  • [6] FURTHER STUDY ON THE ONE-POT SYNTHESIS OF (E)-2-NONENAL FROM CASTOR-OIL
    KULA, J
    SIKORA, M
    DABROWSKI, R
    [J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1994, 71 (05) : 545 - 546
  • [7] CHARACTERISTICS AND COMPOSITION OF NEWER VARIETIES OF INDIAN CASTOR SEED AND OIL
    LAKSHMINARAYANA, G
    PAULOSE, MM
    KUMARI, BN
    [J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1984, 61 (12) : 1871 - 1872
  • [8] STEREOISOMERIC FLAVOR COMPOUNDS .20. STRUCTURE AND PROPERTIES OF GAMMA-LACTONE ENANTIOMERS
    MOSANDL, A
    GUNTHER, C
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1989, 37 (02) : 413 - 418
  • [9] CHANGES IN COMPOSITION OF VOLATILE COMPOUNDS IN HIGH-PRESSURE TREATED PEACH
    SUMITANI, H
    SUEKANE, S
    NAKATANI, A
    TATSUKA, K
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1994, 42 (03) : 785 - 790
  • [10] VOLATILE CONSTITUENTS OF APRICOT (PRUNUS-ARMENIACA)
    TAKEOKA, GR
    FLATH, RA
    MON, TR
    TERANISHI, R
    GUENTERT, M
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1990, 38 (02) : 471 - 477