Synthesis of 2-substituted chromenes via ring-closing metathesis and stable 1-benzopyrylium ions

被引：44

作者：

Doodeman, R

Rutjes, FPJT

Hiemstra, H

机构：

[1] Univ Nijmegen, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands

[2] Univ Amsterdam, Inst Mol Chem, Organ Chem Lab, NL-1018 WS Amsterdam, Netherlands

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 31期

关键词：

benzyloxy-1,2-propadiene; ring-closing metathesis; 1-benzopyrylium ions; chromenes;

D O I：

10.1016/S0040-4039(00)00955-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Substituted chromenes were obtained via combination of ring-closing metathesis of allylic acetals to the corresponding cyclic acetals, followed by Lewis acid-mediated functionalization of the resulting stable 1-benzopyrylium ion with suitable nucleophiles. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5979 / 5983

页数：5

相关论文

共 35 条

[1] UNUSUAL FRIEDEL-CRAFTS REACTIONS .3. SYNTHESIS OF 2,4-DIETHOXYCHROMANS AND THEIR CONVERSION INTO BENZOPYRYLIUM PERCHLORATES [J].

BIGI, F ;

CASIRAGHI, G ;

CASNATI, G ;

SARTORI, G .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (07) :1325-1328

[2] Ring closing metathesis of phenyl-substituted dienes [J].

Bujard, M ;

Briot, A ;

Gouverneur, V ;

Mioskowski, C .

TETRAHEDRON LETTERS, 1999, 40 (50) :8785-8788

[3]

Carda M, 1999, SYNLETT, P1639

[4] A highly efficient and practical synthesis of chromene derivatives using ring-closing olefin metathesis [J].

Chang, SB ;

Grubbs, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :864-866

[5] Synthesis of medium-sized cyclic allylic ethers by ring-closing metathesis and subsequent elaboration to sub-units found in the brevetoxins and ciguatoxins [J].

Clark, JS ;

Hamelin, O ;

Hufton, R .

TETRAHEDRON LETTERS, 1998, 39 (45) :8321-8324

[6] Modern tanning chemistry [J].

Covington, AD .

CHEMICAL SOCIETY REVIEWS, 1997, 26 (02) :111-126

[7] An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin [J].

Crimmins, MT ;

Choy, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5653-5660

[8] Asymmetric total synthesis of callystatin A: Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones [J].

Crimmins, MT ;

King, BW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9084-9085

[9] Ring-closing metathesis in the synthesis of large and medium-sized oxacycles.: Application to the synthesis of polyoxygenated macrocycles [J].

Delgado, M ;

Martín, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4798-4816

[10] Efficient total syntheses of resin glycosides and analogues by ring-closing olefin metathesis [J].

Fürstner, A ;

Müller, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (34) :7814-7821

← 1 2 3 4 →