REARRANGEMENTS OF BRIDGEHEAD BROMIDES - A DIRECT SYNTHESIS OF EPI-MODHEPHENE

被引：25

作者：

KRAUS, GA

SHI, JM

机构：

[1] Department of Chemistry, Iowa State University, Ames

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 20期

关键词：

D O I：

10.1021/jo00307a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of nucleophiles with bridgehead bromides 3 and 4 affords rearrangement products resulting from addition of the nucleophile to the carbonyl group followed by ring contraction. This rearrangement has been employed in a direct synthesis of epi-modhephene. © 1990, American Chemical Society. All rights reserved.

引用

收藏

页码：5423 / 5424

页数：2

相关论文

共 9 条

[1]

CURRAN DP, 1988, SYNTHESIS-STUTTGART, V417, P489

[2]

HEATHCOCK CH, 1971, TETRAHEDRON LETT, P4995

[3] ASYMMETRIC TOTAL SYNTHESIS OF ATISINE VIA INTRAMOLECULAR DOUBLE MICHAEL REACTION [J].

IHARA, M ;

SUZUKI, M ;

FUKUMOTO, K ;

KABUTO, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) :1164-1171

[4] SEQUENTIAL RADICAL CYCLIZATION APPROACH TO PROPELLANE TRIQUINANES - TOTAL SYNTHESIS OF (+/-)-MODHEPHENE [J].

JASPERSE, CP ;

CURRAN, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5601-5609

[5] TOTAL SYNTHESES OF DITERPENES + DITERPENE ALKALOIDS .V. ATISINE [J].

MASAMUNE, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (02) :291-&

[6] TOTAL SYNTHESIS OF MODHEPHENE [J].

MUNDY, BP ;

WILKENING, D ;

LIPKOWITZ, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5727-5731

[7] STEREOSPECIFIC TOTAL SYNTHESIS OF DL-ATISINE [J].

NAGATA, W ;

WAKABAYASHI, T ;

NARISADA, M ;

HAYASE, Y ;

SUGASAWA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (15) :2342-&

[8] MECHANISTIC CHANGES IN A FAVORSKII REACTION [J].

WARNHOFF, EW ;

WONG, CM ;

TAI, WT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (02) :514-&

[9] SOME HIGHLIGHTS IN THE STRUCTURAL AND SYNTHETIC CHEMISTRY OF THE ACONITE ALKALOIDS - A PERSONAL HISTORICAL-PERSPECTIVE [J].

WIESNER, K .

TETRAHEDRON, 1985, 41 (03) :485-497