A convenient synthesis of naturally occurring benzofuran ailanthoidol

被引：71

作者：

Kao, CL ^{[1
]}

Chern, JN ^{[1
]}

机构：

[1] Natl Taiwan Univ, Coll Med, Sch Pharm, Sect 1, Taipei 100, Taiwan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 06期

关键词：

ailanthoidol; benzofuran; trimethylsilyldiazomethane lithium salt; oxymercuration;

D O I：

10.1016/S0040-4039(00)02163-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient method for the synthesis of ailanthoidol starting from vanillin is provided using trimethylsilyldiazomethane lithium salt to generate a diphenylacetylene and subsequent oxymercuration cyclization of the resulting alkyne with mercury acetate in acetic acid as key steps. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1111 / 1113

页数：3

共 18 条

[1]

BATES RW, 1995, SYNLETT, P1151

[2]

COLVIN EW, 1977, J CHEM SOC P1, P1379

[3] A new approach to 2-aryl-7-alkoxy-benzofurans: Synthesis of ailanthoidol, a natural neolignan [J].

Fuganti, C ;

Serra, S .

TETRAHEDRON LETTERS, 1998, 39 (31) :5609-5610

[4] In vivo immunosuppressive activity of some cyclolignans [J].

Gordaliza, M ;

Castro, MA ;

delCorral, JMM ;

LopezVazquez, ML ;

SanFeliciano, A ;

Faircloth, GT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (21) :2781-2786

[5] Immunosuppressive cyclolignans [J].

Gordaliza, M ;

Faircloth, GT ;

Castro, MA ;

delCorral, JMM ;

LopezVazquez, ML ;

SanFeliciano, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) :2865-2868

[6]

Ito Y, 1997, SYNLETT, P1163

[7] Novel selective PDE IV inhibitors as antiasthmatic agents. Synthesis and biological activities of a series of 1-aryl-2,3-bis(hydroxymethyl)naphthalene lignans [J].

Iwasaki, T ;

Kondo, K ;

Kuroda, T ;

Moritani, Y ;

Yamagata, S ;

Sugiura, M ;

Kikkawa, H ;

Kaminuma, O ;

Ikezawa, K .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) :2696-2704

[8] The influence of flaxseed and lignans on colon carcinogenesis and beta-glucuronidase activity [J].

Jenab, M ;

Thompson, LU .

CARCINOGENESIS, 1996, 17 (06) :1343-1348

[9] MERCURY IN ORGANIC-CHEMISTRY .26. SYNTHESIS OF HETEROCYCLES VIA INTRAMOLECULAR SOLVOMERCURATION OF ARYL ACETYLENES [J].

LAROCK, RC ;

HARRISON, LW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4218-4227

[10] ANTIOXIDANT ACTIVITY OF DIBENZOCYCLOOCTENE LIGNANS ISOLATED FROM SCHISANDRACEAE [J].

LU, H ;

LIU, GT .

PLANTA MEDICA, 1992, 58 (04) :311-313

← 1 2 →