Approaches to oximidines, lobatamides and related natural products:: the coupling reactions of 3-iodoacrolein O-methyl oximes

被引:16
作者
Raw, SA [1 ]
Taylor, RJK [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
D O I
10.1016/S0040-4039(00)01862-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both 2E- and 2Z-3-iodoacrolein O-methyl oximes are prepared in two steps from ethyl propiolate. Lithium-iodine exchange is effected and the resulting organolithium reagents added to several electrophiles, including styryl isocyanate which gives a conjugated O-methyl oxime enamide of the type found in the side chains of the oximidine, lobatamide and CJ-12950 natural products. The Pd(0) catalysed cross-coupling of these iodoalkenes is also explored. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10357 / 10361
页数:5
相关论文
共 14 条
[1]   THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ENOL ACETATES OF ALPHA-BROMO KETONES WITH 1-ALKENYLBORON, ARYLBORON, OR ALKYLBORON COMPOUNDS - A FACILE SYNTHESIS OF KETONES AND THEIR ENOL ACETATES [J].
ABE, S ;
MIYAURA, N ;
SUZUKI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (10) :2863-2865
[2]   SYNTHESIS OF ENAMIDES [J].
BRETTLE, R ;
MOSEDALE, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2185-2195
[3]   Novel lactone compounds from Mortierella verticillata that induce the human low density lipoprotein receptor gene:: Fermentation, isolation, structural elucidation and biological activities [J].
Dekker, KA ;
Aiello, RJ ;
Hirai, H ;
Inagaki, T ;
Sakakibara, T ;
Suzuki, Y ;
Thompson, JF ;
Yamauchi, Y ;
Kojima, N .
JOURNAL OF ANTIBIOTICS, 1998, 51 (01) :14-20
[4]   Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. [J].
Erickson, KL ;
Beutler, JA ;
Cardellina, JH ;
Boyd, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8188-8192
[5]  
Jansen R, 2000, EUR J ORG CHEM, V2000, P913, DOI 10.1002/(SICI)1099-0690(200003)2000:6<913::AID-EJOC913>3.0.CO
[6]  
2-L
[7]   Oximidines I and II:: Novel antitumor macrolides from Pseudomonas sp. [J].
Kim, JW ;
Shin-ya, K ;
Furihata, K ;
Hayakawa, Y ;
Seto, H .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :153-155
[8]  
Kuramochi K, 2000, SYNLETT, P397
[9]  
MAREK I, 1996, ORG SYNTH, V74, P194
[10]   The lobatamides, novel cytotoxic macrolides from southwestern Pacific tunicates [J].
McKee, TC ;
Galinis, DL ;
Pannell, LK ;
Cardellina, JH ;
Laakso, J ;
Ireland, CM ;
Murray, L ;
Capon, RJ ;
Boyd, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7805-7810