Total synthesis of (+/-)-rocaglamide and some aryl analogues

Authors
Dobler, MR Bruce, I Cederbaum, F Cooke, NG Diorazio, LJ Hall, RG Irving, E
Citation
Mr. Dobler et al., Total synthesis of (+/-)-rocaglamide and some aryl analogues, TETRAHEDR L, 42(47), 2001, pp. 8281-8284
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
47
Year of publication
2001
Pages
8281 - 8284
Database
ISI
SICI code
0040-4039(20011119)42:47<8281:TSO(AS>2.0.ZU;2-7
Abstract
The insecticidal activity found for rocaglamide and its congeners, prompted us to establish a short and efficient synthesis of the natural product and some synthetic 'halo-aryl' analogues. Pd-catalysed cross-coupling reaction s of the bromo analogue were then explored in order to gain a suitable acce ss to a broad range of unnatural analogues. The key step of our approach is a keto-aldehyde acyloin ring-closure followed by a Stiles carboxylation. ( C) 2001 Elsevier Science Ltd. All rights reserved.