THE SYNTHESIS OF D(6)-ALPHA-FARNESENE

被引:8
作者
FIELDER, S
ROWAN, DD
机构
[1] Horticulture and Food Research Institute of New Zealand Ltd, Palmerston North, 030
关键词
ALPHA-FARNESENE; SYNTHESIS; DEUTERIUM LABELING; SULPHOLENE;
D O I
10.1002/jlcr.2580341111
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
d(6)-alpha-Famesene (3,7-dimethyl-11-H-2(3)-methyl-12,12,12-H-2(3)-dodeca-1,3E,6E,10-tetraene) has been synthesised by two routes. Thermolysis of 2-geranyl-3-methylsulpholene (5) yielded unlabelled alpha-famesene (93%) which was epoxidized at Delta 10 in 31% yield. Oxidative cleavage of the epoxide (42%) and Wittig elaboration of the resultant trienal with d(6)-Isopropyl triphenylphosphorane gave d(6)-alpha-famesene (73%). Alternatively, selective epoxidation of (5) gave the terminal 6',7' mono-epoxide in 74% yield. Oxidative cleavage (73%) and Wittig elaboration of the resultant aldehyde;yielded deuterated 2-geranyl-3-methylsulpholene (46%). Thermal elimination of sulphur dioxide afforded the title compound in 91% yield.
引用
收藏
页码:1075 / 1085
页数:11
相关论文
共 24 条
[1]  
Anet E. F. L. J., 1974, CSIRO Food Research Quarterly, V34, P4
[2]   SUPERFICIAL SCALD, A FUNCTIONAL DISORDER OF STORED APPLES .11. APPLE ANTIOXIDANTS [J].
ANET, EFL .
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 1974, 25 (03) :299-304
[3]   SUPERFICIAL SCALD, A FUNCTIONAL DISORDER OF STORED APPLES .10. CONTROL OF ALPHA-FARNESENE AUTOXIDATION [J].
ANET, EFL ;
COGGIOLA, IM .
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 1974, 25 (03) :293-298
[4]   SYNTHESIS OF (E,Z)-ALPHA-, (Z,Z)-ALPHA-, AND (Z)-BETA-FARNESENE [J].
ANET, EFLJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1970, 23 (10) :2101-&
[5]   CONTROL OF SUPERFICIAL SCALD ON DANJOU PEARS BY ETHOXYQUIN - OXIDATION OF ALPHA-FARNESENE AND ITS INHIBITION [J].
CHEN, PM ;
VARGA, DM ;
MIELKE, EA ;
FACTEAU, TJ ;
DRAKE, SR .
JOURNAL OF FOOD SCIENCE, 1990, 55 (01) :171-&
[6]   CONTROL OF SUPERFICIAL SCALD ON DANJOU PEARS BY ETHOXYQUIN - EFFECT OF ETHOXYQUIN CONCENTRATION, TIME AND METHOD OF APPLICATION, AND A COMBINED EFFECT WITH CONTROLLED-ATMOSPHERE STORAGE [J].
CHEN, PM ;
VARGA, DM ;
MIELKE, EA ;
FACTEAU, TJ ;
DRAKE, SR .
JOURNAL OF FOOD SCIENCE, 1990, 55 (01) :167-170
[7]  
CHOU T, 1984, J CHEM SOC CHEM COMM, P1325
[8]   CONVENIENT SYNTHESES OF HYDROINDANS AND HYDRONAPHTHALENES [J].
CHOU, TS ;
TSO, HH ;
CHANG, LJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (04) :236-237
[9]   AROMA QUALITY EVALUATION OF TOMATOES, APPLES, AND STRAWBERRIES [J].
DIRINCK, P ;
SCHREYEN, L ;
SCHAMP, N .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1977, 25 (04) :759-763
[10]   THE SYNTHESIS OF 4-H-2-ALPHA-FARNESENE AND 1-H-2-ALPHA-FARNESENE [J].
FIELDER, S ;
ROWAN, DD ;
REAY, PF .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1993, 33 (10) :965-975