Rearrangement of a Tricyclic 2,5-Cyclohexadienone: Towards a General Synthetic Route to the Daphnanes and (+)-Resiniferatoxin

Light as a reagent: A highly functionalized structure that serves as a daphnane template can be formed by the photorearrangement of a 2,5‐cyclohexadienone subunit within a complex tricyclic ring system (see scheme). The chemistry we describe should not only find use in the total synthesis of resinif...

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Published inAngewandte Chemie International Edition Vol. 40; no. 14; pp. 2694 - 2697
Main Authors Jackson, Stona R., Johnson, Michael G., Mikami, Masafumi, Shiokawa, Sojiro, Carreira, Erick M.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 16.07.2001
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
photochemistry
Physical Sciences
rearrangement
Science & Technology
synthesis design
synthetic methods
KETONES
PHORBOL
RING-SYSTEM
photochemistry
rearrangement
synthesis design
synthetic methods
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Summary:Light as a reagent: A highly functionalized structure that serves as a daphnane template can be formed by the photorearrangement of a 2,5‐cyclohexadienone subunit within a complex tricyclic ring system (see scheme). The chemistry we describe should not only find use in the total synthesis of resiniferatoxin and related daphnanes, but should also provide useful templates for access to complex analogues.
Bibliography:istex:29AE611586BAA616C08E9294740C8AAFBBC3750F
ArticleID:ANIE2694
ark:/67375/WNG-ZKRQ114K-3
We wish to gratefully acknowledge the support of Daiso Ltd., Japan (M.M.), and Meiji Seika Kaisha Ltd., Japan (S.S.). M.J. thanks Pharmacia‐UpJohn for a graduate fellowship during his third year at Caltech. Financial support was provided by the Packard Foundation, the National Science Foundation (USA), the National Institutes of Health (USA), and by generous funds from Eli Lilly, Merck, Novartis, Pfizer, Pharmacia‐Upjohn, Zeneca, the Eidgenössische Technische Hochschule (ETH), the Kontaktgruppe für Forschungsfragen (KGF), and Hoffmann La Roche.
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010716)40:14<2694::AID-ANIE2694>3.0.CO;2-D