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

[41] SYNTHESES AND INSECTICIDAL ACTIVITY OF 8-ISOPROPYL-6-OXABICYCLO[3.2.1]OCTAN-7-ONE, A PARTIAL SKELETON OF PICROTOXININ, AND RELATED-COMPOUNDS
KUWANO, E
OHSHIMA, K
ETO, M
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1980, 44 (02): : 383 - 386
[42] EFFICIENT SYNTHESIS OF "8-OXABICYCLO[3.2.1]OCT-6-EN-3-ONES, PREPARATIVELY USEFUL [4+3]-CYCLOADDUCTS
FOHLISCH, B
GEHRLACH, E
HERTER, R
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (02): : 137 - 137
[43] Diastereo- and enantioselective synthesis of 2,8-dioxabicyclo[3.3.0]octan-3-one derivatives
Enders, D
Vázquez, J
Raabe, G
CHEMICAL COMMUNICATIONS, 1999, (08) : 701 - 702
[44] 7-ALPHA-FORMYLOXY-8-BETA-FORMYLOXYMETYLENE-CIS-2-OXABICYCLO[3.3.0]OCTAN-3-ONE AS A USEFUL SYNTON FOR PROSTAGLANDINS
TOLSTIKOV, GA
MIFTAKHOV, MS
VALEEV, FA
VOSTRIKOV, NS
AKHMETVALEEV, RR
ZHURNAL ORGANICHESKOI KHIMII, 1984, 20 (01): : 221 - 222
[45] Concise Entry to Both Enantiomers of 8-Oxabicyclo[3.2.1]oct-3-en-2-one Based on Novel Oxidative Etherification: Formal Synthesis of (+)-Sundiversifolide
Kawasumi, Muneo
Kanoh, Naoki
Iwabuchi, Yoshiharu
ORGANIC LETTERS, 2011, 13 (14) : 3620 - 3623
[46] 8-Oxabicyclo[3.2.1]oct-6-en-3-one as a module for the synthesis of beta-alkoxy-delta-valerolactones relevant to natural products and drugs
Dunkel, R
Mentzel, M
Hoffmann, HMR
TETRAHEDRON, 1997, 53 (44) : 14929 - 14936
[47] SYNTHESIS AND POLYMERIZATION OF 3-AZA-8-OXABICYCLO[3.2.1]OCTANE-2-ONE
MOORE, JA
PARTAIN, EM
JOURNAL OF POLYMER SCIENCE PART C-POLYMER LETTERS, 1982, 20 (10) : 521 - 523
[48] Synthesis and studies of marine natural products: the dictyoxetane core from 8-oxabicyclo[3.2.1]oct-6-en-3-ones
Proemmel, S
Wartchow, R
Hoffmann, HMR
TETRAHEDRON, 2002, 58 (31) : 6199 - 6206
[49] Synthesis of 3-(4-heteroaryl-phenyl)-8-oxabicyclo[3.2.1]octane-2-carboxylic acid methyl esters
Torun, L
Liu, SH
Madras, BK
Meltzer, PC
TETRAHEDRON LETTERS, 2006, 47 (04) : 599 - 603
[50] TOTAL SYNTHESIS OF PROSTAGLANDIN-E2 BY REARRANGEMENT OF A 6,8-DISUBSTITUTED-2-OXABICYCLO[3.2.1]OCTAN-3-ONE TO A 4,5-DISUBSTITUTED-PERHYDROCYCLOPENTA[B]FURAN-2-ONE
NEWTON, RF
REYNOLDS, DP
WEBB, CF
YOUNG, SN
GRUDZINSKI, Z
ROBERTS, SM
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (11): : 2789 - 2792

← 1 2 3 4 5 →