Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 1991; 1991(7): 526-528
DOI: 10.1055/s-1991-20788
DOI: 10.1055/s-1991-20788
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
The Intramolecular Diels-Alder Reaction with Furan-Diene: A Novel Route to (±)-Gibberellin A5
Further Information
Publication History
Publication Date:
07 March 2002 (online)
![](https://www.thieme-connect.de/media/synlett/199107/lookinside/thumbnails/10.1055-s-1991-20788-1.jpg)
A novel potential approach to 20-norgibberellins is described and exemplified with the total synthesis of (±)-gibberellin A5 from methyl (1S,2R, 5S)-2-(2-furyl)-5-hydroxy-6-methylenebicyclo[3.2.1]octane-1-carboxylate. Key steps involve an intramolecular Diels-Alder reaction with the furan-diene moiety leading to a kaurenoid analogue and the subsequent ring contraction of the central 5-membered ring to yield the required carboxy-substituted cyclopentane moiety via a photochemical α-diazo ketone Wolff rearrangement.