A new analogue of rocaglamide by an oxidative dihydrofuran synthesis

Authors
Schoop, A Greiving, H Gohrt, A
Citation
A. Schoop et al., A new analogue of rocaglamide by an oxidative dihydrofuran synthesis, TETRAHEDR L, 41(12), 2000, pp. 1913-1916
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
12
Year of publication
2000
Pages
1913 - 1916
Database
ISI
SICI code
0040-4039(20000318)41:12<1913:ANAORB>2.0.ZU;2-U
Abstract
A new analogue of rocaglamide 1 has been synthesised. The tricyclic core st ructure that is lacking the C-8b hydroxy group was generated in an oxidativ e addition of 1,3-cyclohexanedione to a cyclopentene moiety forming a tricy clic dihydrofuran system. Further transformation gave analogue 12 with the desired configuration. Although this C-8b deoxy derivative exhibits no inse cticidal activity, it provides important information in understanding the s tructure-activity relationship. (C) 2000 Elsevier Science Ltd. All rights r eserved.