Synthesis of azaphilones and related molecules by employing cycloisomerization of o-alkynylbenzaldehydes

被引：163

作者：

Zhu, JL ^{[1
]}

Germain, AR ^{[1
]}

Porco, JA ^{[1
]}

机构：

[1] Boston Univ, Ctr Chem Methodol & Lib Dev, Dept Chem, Boston, MA 02215 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 10期

关键词：

alkynes; azaphilones; cycloisomerization; gold; Lewis acid catalysis;

D O I：

10.1002/anie.200353037

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Right to the core: Gold(III)-catalyzed cycloisomerization of o-alkynylbenzaldehydes to 2-benzopyrylium salts and subsequent in situ oxidation have been employed to prepare the core structure of azaphilone natural products, such as the sphingosine kinase inhibitor S-15183 (see scheme, DCE = 1,2-dichloroethane, TFA = trifluoroacetic acid)), and several unnatural azaphilones.

引用

页码：1239 / 1243

页数：5

共 61 条

[1] [Anonymous], 2002, ANGEW CHEM, V114, P1035
[2] [Anonymous], 2002, ANGEW CHEM
[3] AuBr3-catalyzed cyclization of o-(alkynyl)nitrobenzenes.: Efficient synthesis of isatogens and anthranils
Asao, N
Sato, K
Yamamoto, Y
[J]. TETRAHEDRON LETTERS, 2003, 44 (30) : 5675 - 5677
[4] Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes
Asao, N
Kasahara, T
Yamamoto, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) : 3504 - 3506
[5] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes
Asao, N
Nogami, T
Lee, S
Yamamoto, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10921 - 10925
[6] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes
Asao, N
Takahashi, K
Lee, S
Kasahara, T
Yamamoto, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) : 12650 - 12651
[7] Asao T., 2003, ANGEW CHEM, V115, P3628
[8] CHEMISTRY OF FUNGI .62. SYNTHESIS OF (+/-)-MITORUBRIN, A METABOLITE OF PENICILLIUM-RUBRUM
CHONG, R
GRAY, RW
KING, RR
WHALLEY, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (21): : 3571 - &
[9] CHEMISTRY OF FUNGI .61. SYNTHESIS OF (+/-)-SCLEROTIORIN, OF (+/-)-4,6-DIMETHYLOCTA-TRANS-2,TRANS-4-DIENOIC ACID, AND OF AN ANALOGUE OF ROTIORIN
CHONG, R
KING, RR
WHALLEY, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (21): : 3566 - &
[10] Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO

← 1 2 3 4 5 6 7 →