Synthesis of the pseudoguaianolide and guaianolide skeleton by cleavage of the ether bridge of 8-oxabicyclo[3.2.1]octan-3-one derivatives

被引：6

作者：

Rubinger, MMM ^{[1
]}

Mann, J

机构：

[1] Univ Fed Vicosa, Dept Quim, BR-36571000 Vicosa, MG, Brazil

[2] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England

来源：

JOURNAL OF CHEMICAL RESEARCH-S | 1999年 / 07期

关键词：

D O I：

10.1039/a902354b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of three new polysubstituted cycloheptenones by cleavage of the ether bridge of 8-oxabicyclo[3.2.1] octan-3-one derivatives is described, together with the application of this methodology in the construction of the guaianolide and pseudoguaianolide skeleton.

引用

页码：454 / 455

页数：3

共 50 条

[1] CLEAVAGE OF THE OXYGEN BRIDGE IN 8-OXABICYCLO[3.2.1]OCTAN-3-ONES AND 8-OXABICYCLO[3.2.1]OCT-6-EN-3-ONES BY TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE
FOHLISCH, B
SENDELBACH, S
BAUER, H
LIEBIGS ANNALEN DER CHEMIE, 1987, (01): : 1 - 5
[2] Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines.
Simoni, D
Roberti, M
Rondanin, R
Kozikowski, AP
TETRAHEDRON LETTERS, 1999, 40 (23) : 4425 - 4428
[3] ENANTIOSELECTIVE DEPROTONATION OF 8-OXABICYCLO[3.2.1]OCTAN-3-ONE SYSTEMS USING HOMOCHIRAL LITHIUM AMIDE BASES
BUNN, BJ
COX, PJ
SIMPKINS, NS
TETRAHEDRON, 1993, 49 (01) : 207 - 218
[4] Cleavage of the oxygen bridge in 8-oxabicyclo [3.2.1]octanes by reductive elimination
Föhlisch, B
Kreiselmeier, G
TETRAHEDRON, 2001, 57 (51) : 10077 - 10088
[5] 2,4-Dimethyl-6-phenyl-8-oxabicyclo[3.2.1]-octan-3-one
Dockendorff, C
Lautens, M
Lough, AJ
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O1601 - O1603
[6] Asymmetric epoxidation catalyzed by esters of α-hydroxy-8-oxabicyclo[3.2.1]octan-3-one
Armstrong, A
Moss, WO
Reeves, JR
TETRAHEDRON-ASYMMETRY, 2001, 12 (20) : 2779 - 2781
[7] SYNTHESIS OF SOME DERIVATIVES OF 8-ALKYL-8-AZA-BICYCLO[3.2.1]OCTAN-3-ONE
GUTKOWSKA, B
KMIOTEK, R
KWIATKOWSKA, B
ACTA POLONIAE PHARMACEUTICA, 1981, 38 (04): : 411 - 415
[8] NOVEL REACTIONS OF 2-CARBOMETHOXYMETHYL-2-THIOPHENYL-8-OXABICYCLO[3.2.1]OCTAN-3-ONE
RUBINGER, MMM
MANN, J
DREW, MGB
TETRAHEDRON, 1995, 51 (41) : 11295 - 11304
[9] Asymmetric synthesis of highly functionalized 8-oxabicyclo[3.2.1]octene derivatives
Davies, HML
Ahmed, G
Churchill, MR
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) : 10774 - 10782
[10] Asymmetric synthesis of highly functionalized 8-oxabicyclo[3.2.1]-octane derivatives
Ahmed, G
Davies, HML
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 298 - ORGN

← 1 2 3 4 5 →