A mild, efficient and general method for the synthesis of trialkylsilyl (Z)-4-oxo-2-alkenoates and γ-hydroxybutenolides

被引：45

作者：

Boukouvalas, J ^{[1
]}

Lachance, N ^{[1
]}

机构：

[1] Univ Laval, Dept Chim, Quebec City, PQ G1K 7P4, Canada

来源：

SYNLETT | 1998年 / 01期

关键词：

gamma-hydroxybutenolides; trialkylsilyl (Z)-4-oxo-2-alkenoates; 2-trialkylsilyloxyfurans; dimethyldioxirane; oxidation;

D O I：

10.1055/s-1998-1574

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Trialkylsilyloxyfurans react rapidly with dimethyldioxirane at -78 degrees C to provide trialkylsilyl (Z)-4-oxo-2-alkenoates whose hydrolysis delivers gamma-hydroxybutenolides with high efficiency; a short synthesis of a naturally occurring monoterpene gamma-hydroxybutenolide (4) is reported.

引用

页码：31 / +

页数：3

共 49 条

[31] SINGLET OXYGEN OXIDATION OF SUBSTITUTED FURANS TO 5-HYDROXY-2(5H)-FURANONE
LEE, GCM
SYAGE, ET
HARCOURT, DA
HOLMES, JM
GARST, ME
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) : 7007 - 7014
[32] Enantioselective synthesis of (R)- and (S)-2-alkyl-1,4-butanediols via enantiomerically pure 3-alkyl-5-(menthyloxy)butyrolactones
Lee, N
Kim, YW
Chang, K
Kim, KH
Jew, SS
Kim, DK
[J]. TETRAHEDRON LETTERS, 1996, 37 (14) : 2429 - 2432
[33] Vinylogous Mannich reactions. The asymmetric total synthesis of (+)-croomine
Martin, SF
Barr, KJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (13) : 3299 - 3300
[34] Murray RW, 1997, ORG SYNTH, V74, P91
[35] EVIDENCE FOR THE FORMATION OF HETEROCYCLIC ARENE OXIDES AND A GAMMA-KETO ENAL BY REACTION OF MENTHOFURAN WITH DIMETHYLDIOXIRANE
OISHI, S
NELSON, SD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) : 2744 - 2747
[36] CAROTENOIDS AND RELATED COMPOUNDS .18. SYNTHESIS OF CIS- AND DI-CIS-POLYENES BY REACTIONS OF WITTIG TYPE
PATTENDEN, G
WEEDON, BCL
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (16): : 1984 - +
[37] RECENT PROGRESS IN COMMERCIAL RETINOIDS AND CAROTENOIDS
PAUST, J
[J]. PURE AND APPLIED CHEMISTRY, 1991, 63 (01) : 45 - 58
[38] STEREOSELECTIVE TOTAL SYNTHESIS OF THE MARINE SESTERTERPENOID (+/-)-PALAUOLIDE
PIERS, E
WAI, JSM
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (01): : 146 - 157
[39] Pommier A., 1997, J CHEM SOC CHEM COMM, P1139
[40] CHEMICAL MECHANISM OF INACTIVATION OF BEE VENOM PHOSPHOLIPASE-A2 BY THE MARINE NATURAL-PRODUCTS MANOALIDE, LUFFARIELLOLIDE, AND SCALARADIAL
POTTS, BCM
FAULKNER, DJ
DECARVALHO, MS
JACOBS, RS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 5093 - 5100

← 1 2 3 4 5 →