A new analogue of rocaglamide by an oxidative dihydrofuran synthesis

A new analogue of rocaglamide 1 has been synthesised. The tricyclic core structure that is lacking the C-8b hydroxy group was generated in an oxidative addition of 1,3-cyclohexanedione to a cyclopentene moiety forming a tricyclic dihydrofuran system. Further transformation gave analogue 12 with the...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 12; pp. 1913 - 1916
Main Authors Schoop, Andreas, Greiving, Helmut, Göhrt, Axel
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.03.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AGLAIA-ODORATA
DERIVATIVES
CYCLIZATION
Online AccessGet full text

Cover

More Information
Summary:A new analogue of rocaglamide 1 has been synthesised. The tricyclic core structure that is lacking the C-8b hydroxy group was generated in an oxidative addition of 1,3-cyclohexanedione to a cyclopentene moiety forming a tricyclic dihydrofuran system. Further transformation gave analogue 12 with the desired configuration. Although this C-8b deoxy derivative exhibits no insecticidal activity, it provides important information in understanding the structure–activity relationship.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00021-6