AN ACYLNITROSO CYCLOADDITION APPROACH TO THE SYNTHESIS OF HIGHLY OXYGENATED INDOLIZIDINE ALKALOIDS

被引：64

作者：

KECK, GE

ROMER, DR

机构：

[1] Department of Chemistry, University of Utah, Salt Lake City

[2] Dow Chemical, Midland, MI 48674

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 22期

关键词：

D O I：

10.1021/jo00074a040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described. A key feature of the approach is intramolecular [4 + 2] cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine. The requisite intermediates were prepared in optically pure form froM L-glutamic acid.

引用

页码：6083 / 6089

页数：7

共 38 条

[1] AUSTIN GN, 1987, TETRAHEDRON, V43, P3095
[2] A SHORT, ENANTIOSELECTIVE SYNTHESIS OF (-)-SWAINSONINE
BENNETT, RB
CHOI, JR
MONTGOMERY, WD
CHA, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2580 - 2582
[3] TOTAL SYNTHESIS OF DL-CEPHALOTAXINE - THE 1ST EXAMPLE OF AN INTRAMOLECULAR 4 + 2 CYCLO-ADDITION WHERE THE DIENOPHILE HAS BEEN DELIVERED FROM THE FACE OPPOSITE TO THE TETHERING MOIETY
BURKHOLDER, TP
FUCHS, PL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) : 2341 - 2342
[4] COLGATE SM, 1979, AUST J CHEM, V32, P2257
[5] ALPHA-ACYLAMINO RADICAL CYCLIZATIONS - APPLICATION TO THE SYNTHESIS OF (-)-SWAINSONINE
DENER, JM
HART, DJ
RAMESH, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) : 6022 - 6030
[6] INHIBITION OF HUMAN HT29 COLON-CARCINOMA GROWTH-INVITRO AND INVIVO BY SWAINSONINE AND HUMAN INTERFERON-ALPHA-2
DENNIS, JW
KOCH, K
BECKNER, D
[J]. JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1989, 81 (13) : 1028 - 1033
[7] DIBELLO IC, 1989, BIOCHEM J, V259, P855
[8] DOLITTLE RE, 1980, J CHEM ECOL, V6, P473
[9] DORING PR, 1978, NEUROPATH APPL NEURO, V4, P285
[10] Dorling P., 1983, Biochemical Society Transactions, V11, P717

← 1 2 3 4 →