Synthesis of functionalized p-dihydrobenzoquinones and p-benzoquinones based on [3+3] cyclizations of 1,3-bis-silyl enol ethers

被引：19

作者：

Ahmed, Z

Fischer, C

Spannenberg, A

Langer, P

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

TETRAHEDRON | 2006年 / 62卷 / 20期

关键词：

cyclization; dihydroquinones; oxidation; quinones; silyl enol ethers;

D O I：

10.1016/j.tet.2006.03.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized mono-protected p-dihydrobenzoquinones were prepared by [3+3] cyclization of 1,3-bis-silyl enol ethers with 2-acyloxy-3-(silyloxy)alk-2-en-1-ones. Deprotection and oxidation of the products afforded the corresponding p-benzoquinones. (c) 2006 Elsevier Ltd. All rights reserved.

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收藏

页码：4800 / 4806

页数：7

相关论文

共 33 条

[1] Synthesis of functionalized 4-chlorophenols and 1,4-dihydroquinones by [3+3] cyclization of 1,3-bis-silyl enol ethers with 2-chloro- and 2-acyloxy-3-(silyloxy)alk-2-en-1-ones [J].

Ahmed, Z ;

Langer, P .

TETRAHEDRON LETTERS, 2006, 47 (04) :417-419

[2] Polyprenylated phloroglucinol derivatives from Hypericum erectum [J].

An, TY ;

Shan, MD ;

Hu, LH ;

Liu, SJ ;

Chen, ZL .

PHYTOCHEMISTRY, 2002, 59 (04) :395-398

[3] Domino "[3+3]-cyclization-homo-Michael" reactions of 1,3-bissilyl enol ethers with 1,1-diacylcyclopropanes [J].

Bose, G ;

Nguyen, VTH ;

Ullah, E ;

Lahiri, S ;

Görls, H ;

Langer, P .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (26) :9128-9134

[4] CHEMISTRY OF ENOL SILYL ETHERS - A GENERAL-SYNTHESIS OF 3-HYDROXYHOMOPHTHALATES AND A BIOMIMETIC SYNTHESIS OF SCLERIN .12. [J].

BROWNBRIDGE, P ;

CHAN, TH ;

BROOK, MA ;

KANG, GJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (04) :688-693

[5] CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].

CHAN, TH ;

BROWNBRIDGE, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538

[6] An unusual sesquiterpene derivative from the Caribbean gorgonian Pseudopterogoriga rigida [J].

D'Armas, HT ;

Mootoo, BS ;

Reynolds, WF .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11) :1593-1595

[7] Synthesis of functionalized acetophenones by [3+3] cyclizations of 1,3-bis-silyl enol ethers with 2-acetyl-3-silyloxyalk-2-en-1-ones [J].

Dede, R ;

Langer, P .

TETRAHEDRON LETTERS, 2004, 45 (50) :9177-9179

[8] DYE-SENSITIZED PHOTOOXIDATION OF VITAMIN-E REVISITED - NEW 7-OXASPIRO[4.5]DEC-1-ENE-3,6-DIONE PRODUCTS BY OXYGENATION AND RING CONTRACTION OF ALPHA-TOCOPHEROL [J].

DISCHIA, M ;

COSTANTINI, C ;

PROTA, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8353-8356

[9] 2 NEW DIPHENYL ETHERS AND A NEW DEPSIDE FROM THE LICHEN MICAREA-PRASINA FR [J].

ELIX, JA ;

JONES, AJ ;

LAJIDE, L ;

COPPINS, BJ ;

JAMES, PW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (11) :2349-2364

[10]

FUGMANN W, 1997, ROMPP LEXIKOON NATUR

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