STEREOSELECTIVE SYNTHESIS OF (+/-)-(CIS-6-METHYLTETRAHYDROPYRAN-2-YL)ACETIC ACID

被引:10
作者
VARELIS, P
GRAHAM, AJ
JOHNSON, BL
SKELTON, BW
WHITE, AH
机构
[1] UNIV WESTERN AUSTRALIA,DEPT CHEM,NEDLANDS,WA 6009,AUSTRALIA
[2] CURTIN UNIV,WESTERN AUSTRALIAN SCH MINES,KALGOORLIE,WA 6430,AUSTRALIA
关键词
D O I
10.1071/CH9941735
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title compound (1) has been synthesized in seven steps and in 42% overall yield from the nucleophilic diene (2). The relative configuration of (1) has been confirmed by a single-crystal X-ray study.
引用
收藏
页码:1735 / 1739
页数:5
相关论文
共 22 条
[1]   SYNTHESIS OF THE CIVET CONSTITUENT CIS-(6-METHYLTETRAHYDROPYRAN-2-YL)ACETIC ACID [J].
BATES, HA ;
DENG, PN .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4479-4481
[2]   LEWIS ACID MEDIATED CONDENSATION OF ALKENOLS AND ALDEHYDES - A SELECTIVE SYNTHESIS OF TETRAHYDROPYRANS AND OXEPANES [J].
COPPI, L ;
RICCI, A ;
TADDEI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :911-913
[3]   A SIMPLE SYNTHESIS OF DL-CHALCOSE [J].
DANISHEFSKY, S ;
KERWIN, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (08) :1597-1598
[4]   USEFUL DIENE FOR DIELS-ALDER REACTION [J].
DANISHEFSKY, S ;
KITAHARA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7807-7808
[5]  
GALLAGHER T, 1984, J AM CHEM SOC, V106, P1496
[6]   LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].
GEMAL, AL ;
LUCHE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459
[7]   SELECTIVE DEOXYGENATION OF UNSATURATED CARBOHYDRATES WITH PD(0)/PH2SIH2/ZNCL2 - TOTAL SYNTHESIS OF (+)-(S,S)-(6-METHYLTETRAHYDROPYRAN-2-YL)ACETIC ACID [J].
GREENSPOON, N ;
KEINAN, E .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3723-3731
[8]  
HALL SR, 1988, XTAL 2 4 REFERENCE M
[9]   SYNTHESIS AND REACTIONS OF ENANTIOMERICALLY PURE MOLYBDENUM PI-COMPLEXES OF 2H-PYRAN - A GENERAL-APPROACH TO THE ENANTIOSPECIFIC SYNTHESIS OF CIS-2,5-DISUBSTITUTED 5,6-DIHYDRO-2H-PYRANS AND CIS-2,6-DISUBSTITUTED TETRAHYDROPYRANS [J].
HANSSON, S ;
MILLER, JF ;
LIEBESKIND, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9660-9661
[10]   THE CONVERGENT SYNTHESIS OF POLYETHER IONOPHORE ANTIBIOTICS - AN APPROACH TO THE SYNTHESIS OF THE MONENSIN TETRAHYDROPYRAN BIS(TETRAHYDROFURAN) VIA THE ESTER ENOLATE CLAISEN REARRANGEMENT AND REDUCTIVE DECARBOXYLATION [J].
IRELAND, RE ;
NORBECK, DW ;
MANDEL, GS ;
MANDEL, NS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (11) :3285-3294