SYNTHETIC STUDIES TOWARDS BATRACHOTOXIN .1. A FURAN-BASED INTRAMOLECULAR DIELS-ALDER ROUTE TO CONSTRUCT THE A-D RING-SYSTEM

被引：45

作者：

GRINSTEINER, TJ ^{[1
]}

KISHI, Y ^{[1
]}

机构：

[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 45期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)74400-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective intramolecular Diels-Alder reaction has been developed using annelated furans to produce functionalized steroidal nuclei, which can serve as advanced intermediates in the synthesis of batrachotoxin.

引用

页码：8333 / 8336

页数：4

共 21 条

[1] BATRACHOTOXININ-A 20-ALPHA-BENZOATE - A NEW RADIOACTIVE LIGAND FOR VOLTAGE SENSITIVE SODIUM-CHANNELS [J].

BROWN, GB ;

TIESZEN, SC ;

DALY, JW ;

WARNICK, JE ;

ALBUQUERQUE, EX .

CELLULAR AND MOLECULAR NEUROBIOLOGY, 1981, 1 (01) :19-40

[2]

Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01

[3] BATRACHOTOXIN . ACTIVE PRINCIPLE OF COLOMBIAN ARROW POISON FROG PHYLLOBATES BICOLOR [J].

DALY, JW ;

WITKOP, B ;

BOMMER, P ;

BIEMANN, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (01) :124-&

[4]

Grisebach H., 1982, PROGR CHEM NATURAL P, V41, P206

[5]

HUDSON P, 1993, TETRAHEDRON LETT, V45, P7295

[6] STEREOSELECTIVE TOTAL SYNTHESIS OF TESTOSTERONE AND ANDROSTERONE VIA A/B-RING CONSTRUCTION OF THE STEROIDAL RING-SYSTEM BY INTRAMOLECULAR DIELS-ALDER REACTION [J].

IHARA, M ;

SUDOW, I ;

FUKUMOTO, K ;

KAMETANI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (01) :117-123

[7]

IMHOF R, 1972, HELV CHIM ACTA, V45, P1151

[8]

IMHOF R, 1973, HELV CHIM ACTA, V46, P139

[9] STRUCTURAL EFFECTS ON INTRAMOLECULAR FURAN CYCLO-ADDITIONS [J].

KLEIN, LL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1770-1773

[10] STUDIES ON THE SYNTHESIS OF BATRACHOTOXIN [J].

MAGNUS, P ;

LEAPHEART, T ;

WALKER, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (17) :1185-1186

← 1 2 3 →