A RING CONTRACTION OF 6-ALKOXY-2,3-DIHYDRO-6H-PYRAN-3-ONES TO POLYFUNCTIONALIZED CYCLOPENTENONES

被引：20

作者：

KOLB, HC ^{[1
]}

HOFFMANN, HMR ^{[1
]}

机构：

[1] UNIV HANNOVER,DEPT ORGAN CHEM,SCHNEIDERBERG 1B,W-3000 HANNOVER,GERMANY

来源：

TETRAHEDRON | 1990年 / 46卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)87820-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rearrangement of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (1) to trans-4-alkoxy-5-hydroxy-2-cyclopenten-1-ones (2) has been optimized. The effect of buffer concentration (PhCO2 H/KOAc) on reaction rate and yield suggests specific acid catalysis. Substitution patterns and influence of the 6-alkoxy substituent have been investigated. Applications in natural product synthesis are described. © 1990.

引用

页码：5127 / 5144

页数：18

共 23 条

[1] STEREOSPECIFIC SYNTHESIS OF METHYL D,L-HEX-2-ULOPYRANOSIDES FROM FURAN COMPOUNDS
ACHMATOWICZ, O
BURZYNSKA, MH
[J]. TETRAHEDRON, 1982, 38 (23) : 3507 - 3513
[2] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES
ACHMATOWICZ, O
BUKOWSKI, P
SZECHNER, B
ZWIERZCHOWSKA, Z
ZAMOJSKI, A
[J]. TETRAHEDRON, 1971, 27 (10) : 1973 - +
[3] ALTENBACH HJ, 1990, ANGEW CHEM, V102, P64
[4] AN ASYMMETRIC-SYNTHESIS OF CIS-4-TERT-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-OL AND CIS-4-TETRAHYDROPYRANYLOXY-2-CYCLOPENTEN-1-OL, VERSATILE CHIRAL SYNTHETIC INTERMEDIATE FOR PROSTANOIDS
ASAMI, M
[J]. TETRAHEDRON LETTERS, 1985, 26 (47) : 5803 - 5806
[5] SYNTHESIS OF TERREIN, A METABOLITE OF ASPERGILLUS-TERREUS
AUERBACH, J
WEINREB, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (08) : 298 - 299
[6] PHOTOCHEMICAL-TRANSFORMATIONS .35. SIMPLE SYNTHESIS OF RACEMIC TERREIN
BARTON, DHR
HULSHOF, LA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (09): : 1103 - 1106
[7] OXIDATION OF SELENIDES TO SELENOXIDES USING 2-SULFONYLOXAZIRIDINES
DAVIS, FA
STRINGER, OD
BILLMERS, JM
[J]. TETRAHEDRON LETTERS, 1983, 24 (12) : 1213 - 1216
[8] APPLICATIONS OF OXAZIRIDINES IN ORGANIC-SYNTHESIS
DAVIS, FA
SHEPPARD, AC
[J]. TETRAHEDRON, 1989, 45 (18) : 5703 - 5742
[9] GILL M, 1979, TETRAHEDRON LETT, P1539
[10] CHEMISTRY OF SOME METHYL ANHYDROGLYCOSIDULOSES
HAJIVARNAVA, GS
OVEREND, WG
WILLIAMS, NR
[J]. CARBOHYDRATE RESEARCH, 1976, 49 (JUL) : 93 - 102

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