Intramolecular Friedel-Crafts alkylation promoted by the cross conjugated β-keto ester system.: An efficient approach to highly functionalized hydrophenanthrenes and hydrochrysenes.

被引：16

作者：

Liu, HJ ^{[1
]}

Tran, DDP

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30034, Taiwan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 20期

关键词：

Friedel-Crafts alkylation; cross conjugated beta-keto ester system; hydrophenanthrene and hydrochrysene systems;

D O I：

10.1016/S0040-4039(99)00658-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The cross conjugated beta-keto ester system was shown to be an excellent promoter for the intramolecular Friedel-Crafts alkylation to facilitate the rapid construction of highly functionalized phenanthrene and chrysene derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3827 / 3830

页数：4

相关论文

共 14 条

[1]

BARTLETT PA, 1984, ASYMMETRIC SYNTHESIS, V3, P341

[2]

SYNTHESIS OF 15-DEOXY-16-BETA-ETHOXYBRUCEANTIN AND SYNTHETIC EFFORTS TOWARD BRUCEANTIN [J].

CHIU, CKF ;

GOVINDAN, SV ;

FUCHS, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :311-323

[3]

DEV S, 1989, HDB TERPENOIDS, V1, P529

[4]

SYNTHESIS AND CONFIGURATIONAL ASSIGNMENT OF GEIPARVARIN - A NOVEL ANTI-TUMOR AGENT [J].

JERRIS, PJ ;

SMITH, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (03) :577-585

[5]

JOHNSON WS, 1976, BIOORG CHEM, V5, P51, DOI 10.1016/0045-2068(76)90016-X

[6]

REGIOSELECTIVE OLEFIN INSERTION IN ASYMMETRIC HECK REACTION - CATALYTIC ASYMMETRIC-SYNTHESIS OF A VERSATILE INTERMEDIATE FOR DITERPENE SYNTHESES [J].

KONDO, K ;

SODEOKA, M ;

SHIBASAKI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) :4322-4323

[7]

An efficient procedure for the synthesis of thiophene-containing polycyclic compounds via polyene cyclization promoted by the cross conjugated beta-keto ester system [J].

Liu, HJ ;

Tran, DDP .

TETRAHEDRON LETTERS, 1997, 38 (37) :6501-6504

[8]

Polyene cyclization promoted by the cross conjugated alpha-carbalkoxy enone system [J].

Liu, HJ ;

Sun, DQ ;

Shia, KS .

TETRAHEDRON LETTERS, 1996, 37 (45) :8073-8076

[9]

Polyene cyclization promoted by the cross conjugated alpha-carbalkoxy enone system. Application to the total synthesis of (+/-)-dehydrochamaecynenol [J].

Liu, HJ ;

Sun, DQ .

TETRAHEDRON LETTERS, 1997, 38 (35) :6159-6162

[10]

Use of conjugated dienones in cyclialkylations: Total syntheses of arucadiol, 1,2-didehydromiltirone, (+/-)-hinokione, (+/-)-nimbidiol, sageone, and miltirone [J].

Majetich, G ;

Liu, S ;

Fang, J ;

Siesel, D ;

Zhang, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6928-6951