MACROCYCLIZATION THROUGH RADICAL-MEDIATED VINYLCYCLOPROPANE ALKENE CONDENSATION - FACILE ENTRY INTO THE BREFELDIN RING-SYSTEM

被引：36

作者：

FELDMAN, KS ^{[1
]}

BERVEN, HM ^{[1
]}

ROMANELLI, AL ^{[1
]}

PARVEZ, M ^{[1
]}

机构：

[1] UNIV CALGARY, DEPT CHEM, CALGARY T2N 1N4, ALBERTA, CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 24期

关键词：

D O I：

10.1021/jo00076a056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic products featuring an 11-membered ring fused to a core vinylcyclopentane unit are produced upon treatment of functionalized vinylcyclopropanes bearing an omega-alkene unit with a catalytic amount of phenylthio radical. This intramolecular extension of a radical-mediated vinylcyclopropane/alkene cyclocondensation proceeds with only modest diastereoselectivity. The reaction products resemble members of the brefeldin family of naturally occurring antibiotics.

引用

页码：6851 / 6856

页数：6

共 53 条

[1] RADICAL REACTIONS IN SYNTHESIS - INTRAMOLECULAR SH2' MACROCYCLISATIONS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

MITCHELL, MB ;

ROBERTSON, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (22) :1574-1575

[2] INTRAMOLECULAR SH2' MACROCYCLIZATIONS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

MITCHELL, MB ;

ROBERTSON, J .

TETRAHEDRON, 1991, 47 (30) :5901-5918

[3] CYANEIN, A NEW ANTIBIOTIC FROM PENICILLIUM-CYANEUM [J].

BETINA, V ;

BARATH, Z ;

NEMEC, P ;

DOBIAS, J .

FOLIA BIOLOGICA, 1962, 7 (06) :353-&

[4] STRUCTURE-ACTIVITY-RELATIONSHIPS AMONG MYCOTOXINS [J].

BETINA, V .

CHEMICO-BIOLOGICAL INTERACTIONS, 1989, 71 (2-3) :105-146

[5] INTRAMOLECULAR ACYL RADICAL ALKENE ADDITION-REACTIONS - MACROCYCLIZATION REACTIONS [J].

BOGER, DL ;

MATHVINK, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4008-4011

[6] COMPARTMENTATION OF THE GOLGI-COMPLEX - BREFELDIN-A DISTINGUISHES TRANS-GOLGI CISTERNAE FROM THE TRANS-GOLGI NETWORK [J].

CHEGE, NW ;

PFEFFER, SR .

JOURNAL OF CELL BIOLOGY, 1990, 111 (03) :893-899

[7] A SIMPLIFIED SYNTHESIS OF (+)-BREFELDIN-A [J].

COREY, EJ ;

CARPINO, P .

TETRAHEDRON LETTERS, 1990, 31 (52) :7555-7558

[8]

COREY EJ, 1976, TETRAHEDRON LETT, P4701

[9]

COREY EJ, 1976, TETRAHEDRON LETT, P4705

[10]

COREY EJ, 1977, TETRAHEDRON LETT, P2243

← 1 2 3 4 5 6 →