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

Authors
Raw, SA Taylor, RJK
Citation
Sa. Raw et Rjk. Taylor, Approaches to oximidines, lobatamides and related natural products: the coupling reactions of 3-iodoacrolein O-methyl oximes, TETRAHEDR L, 41(52), 2000, pp. 10357-10361
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
52
Year of publication
2000
Pages
10357 - 10361
Database
ISI
SICI code
0040-4039(200012)41:52<10357:ATOLAR>2.0.ZU;2-G
Abstract
Both 2E- and 2Z-3-iodoacrolein O-methyl oximes are prepared in two steps fr om ethyl propiolate. Lithium-iodine exchange is effected and the resulting organolithium reagents added to several electrophiles, including styryl iso cyanate which gives a conjugated O-methyl oxime enamide of the type found i n the side chains of the oximidine, lobatamide and CJ-12950 natural product s. The Pd(0) catalysed cross-coupling of these iodoalkenes is also explored . (C) 2000 Elsevier Science Ltd. All rights reserved.