TOTAL SYNTHESIS OF (+)-HOMOPUMILIOTOXIN 223G

Authors
AOYAGI S HASEGAWA Y HIRASHIMA S KIBAYASHI C
Citation
S. Aoyagi et al., TOTAL SYNTHESIS OF (+)-HOMOPUMILIOTOXIN 223G, Tetrahedron letters, 39(15), 1998, pp. 2149-2152
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
15
Year of publication
1998
Pages
2149 - 2152
Database
ISI
SICI code
0040-4039(1998)39:15<2149:TSO(2>2.0.ZU;2-0
Abstract
A new practical route for the first total synthesis of (+)-homopumilio toxin 223G is described, in which the palladium-catalyzed carbonylatio n of the vinyl iodide, leading to efficient construction of the quinol izidine nucleus incorporating the (Z)-alkylidene side chain, is the ke y strategic element. Another key feature of this synthesis involves th e Lewis acid-induced chelation-controlled propargylation using the all enylsilane with complete diastereoselectivity. (C) 1998 Elsevier Scien ce Ltd. All rights reserved.