Towards the total synthesis of gedunin: construction of the fully elaborated ABC ring system

Pinkerton, David M., Bernhardt, Paul V., Savage, G. Paul and Williams, Craig M. (2017) Towards the total synthesis of gedunin: construction of the fully elaborated ABC ring system. Asian Journal of Organic Chemistry, 6 5: 583-597. doi:10.1002/ajoc.201700013


Author Pinkerton, David M.
Bernhardt, Paul V.
Savage, G. Paul
Williams, Craig M.
Title Towards the total synthesis of gedunin: construction of the fully elaborated ABC ring system
Journal name Asian Journal of Organic Chemistry   Check publisher's open access policy
ISSN 2193-5815
2193-5807
Publication date 2017-03-08
Sub-type Article (original research)
DOI 10.1002/ajoc.201700013
Open Access Status Not yet assessed
Volume 6
Issue 5
Start page 583
End page 597
Total pages 16
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Language eng
Abstract The widely occurring tetranortriterpene natural product gedunin has a well-established range of important biological properties. Although this molecule has received substantial semi-synthetic attention from medicinal chemists, it has not received devoted de novo synthetic attention since it was first isolated in 1960. A key feature of the approach presented herein was the decision to utilize a Robinson annulation reaction, which facilitated the installation of the challenging 7-acetoxy functional group and the completion of the fully functionalized ABC ring system.
Keyword Catalytic hydrogenation
Total synthesis
Natural products
Gedunin
Epoxidation
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 10 Mar 2017, 15:43:05 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences