NDLI: The Intramolecular Diels-Alder Reaction with Furan-Diene: A Novel Route to (±)-Gibberellin $A

Content Provider	Scilit
Author	Nuyttens, Frank Appendino, Giovanni
Editor	Clercq, Pierre J. De
Copyright Year	1991
Description	A novel potential approach to 20-norgibberellins is described and exemplified with the total synthesis of (±)-gibberellin $A_{5}$ 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.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-1991-20788.pdf
Ending Page	528
Page Count	3
Starting Page	526
ISSN	09365214
e-ISSN	14372096
DOI	10.1055/s-1991-20788
Journal	Synlett
Issue Number	07
Volume Number	1991
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	1991-01-01
Access Restriction	Open
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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The Intramolecular Diels-Alder Reaction with Furan-Diene: A Novel Route to (±)-Gibberellin $A_{5}$