Application of directed metallation in synthesis.: Part 3:: Studies in the synthesis of (±)-semivioxanthin and its analogues

被引：34

作者：

Kamila, S ^{[1
]}

Mukherjee, C ^{[1
]}

Mondal, SS ^{[1
]}

De, A ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, W Bengal, India

来源：

TETRAHEDRON | 2003年 / 59卷 / 08期

关键词：

semivioxanthin; naphthopyrone; benzothienopyrone; directed metallation;

D O I：

10.1016/S0040-4020(02)01599-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of several analogues of (+/-)-semivioxanthin including five thiophene analogues, using directed metalation are reported. The strategy consisted of the synthesis of functionalized naphthalene or benzo[b]thiophene as building blocks followed by annelation of the pyrone. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1339 / 1348

页数：10

共 20 条

[1]

Cannon J. G, 1995, BURGERS MED CHEM DRU, P783

[2] ORTHO-METALATED AROMATIC TERTIARY AMIDES - NEW SYNTHETIC APPLICATIONS [J].

CASAS, R ;

CAVE, C ;

DANGELO, J .

TETRAHEDRON LETTERS, 1995, 36 (07) :1039-1042

[3] AN IMPROVED SYNTHESIS OF SUBSTITUTED BENZO[B]THIOPHEN-2-CARBOXYLIC ACIDS AND RELATED ACIDS [J].

CHAKRABA.PM ;

CHAPMAN, NB ;

CLARKE, K .

TETRAHEDRON, 1969, 25 (14) :2781-&

[4] SYNTHESIS OF SULFUR ANALOG OF PSILOCIN AND SOME RELATED COMPOUNDS [J].

CHAPMAN, NB ;

SCROWSTO.RM ;

SUTTON, TM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (23) :3011-3015

[5] Simple Syntheses of (+)-orthosporin and (-)-semivioxanthin methyl ether [J].

Deshpande, VH ;

Rai, B ;

Khan, RA .

TETRAHEDRON, 1996, 52 (20) :7159-7162

[6] SYNTHESIS OF SEMIVIOXANTHIN [J].

DESHPANDE, VH ;

KHAN, RA ;

RAI, B ;

AYYANGAR, NR .

SYNTHETIC COMMUNICATIONS, 1993, 23 (17) :2337-2345

[7]

DESVOYE ML, 1965, B SOC CHIM FR, P1443

[8] Application of directed metallation in synthesis: total synthesis of model compounds related to semivioxanthin [J].

Kamila, S ;

Mukherjee, C ;

De, A .

TETRAHEDRON LETTERS, 2001, 42 (34) :5955-5957

[9] STUDIES IN DEHYDROGENATION OF 6-METHOXY-1-TETRALONE . STRUCTURE OF A NOVEL PRODUCT FORMED WITH TETRACHLORO-1,2-BENZOQUINONE [J].

KASTURI, TR ;

ARUNACHA.T .

CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (23) :3625-&

[10] Studies in sulfur heterocycles.: Part 14.: Application of heteroatom directed ortho-metallation in functionalisation of benzo[b]thiophene derivatives [J].

Mandal, SS ;

Samanta, SS ;

Deb, C ;

De, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (16) :2559-2562

← 1 2 →