Published February 12, 2018
| Supplemental Material
Journal Article
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Total Synthesis of (±)-Phomoidride D
Chicago
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Abstract
Described herein is a synthetic strategy for the total synthesis of (±)‐phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels–Alder cycloaddition. A subsequent SmI2‐mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.
Additional Information
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Issue Online: 06 February 2018; Version of Record online: 17 January 2018; Accepted manuscript online: 29 December 2017; Manuscript received: 02 December 2017. The authors gratefully acknowledge support of this work from Bristol‐Myers Squibb, Eli Lilly, Glaxo‐Wellcome, Yamanouchi (now Astellas), AstraZeneca, and Amgen through their faculty award programs, and the Camille and Henry Dreyfus Foundation for a Teacher Scholar Award to J.W. J.T.N. thanks the Helgu and Jónsdóttur and Sigurliða Kristjánsson Memorial Foundation, G.K.M. thanks the NSERC of Canada, T.S. thanks Prof. Satoshi Ōmura and the Kitasato Institute, and N.T. thanks Yamanouchi (now Astellas). The authors thank Prof. Kevin Klausmeyer and Ms. Sam Yruegas for obtaining and analyzing X‐ray crystallographic data. We also gratefully acknowledge financial support from Baylor University, the Welch Foundation (Chair, AA‐006), and the Cancer Prevention and Research Institute of Texas (CPRIT, R1309). The authors declare no conflict of interest.Attached Files
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Additional details
- Eprint ID
- 102553
- Resolver ID
- CaltechAUTHORS:20200415-101219737
- Bristol-Myers Squibb
- Eli Lilly
- Glaxo‐Wellcome
- Yamanouchi
- Astellas
- AstraZeneca
- Amgen
- Camille and Henry Dreyfus Foundation
- Helgu and Jónsdóttur Memorial Foundation
- Sigurliða Kristjánsson Memorial Foundation
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Kitasato Institute
- Baylor University
- Robert A. Welch Foundation
- AA‐006
- Cancer Prevention and Research Institute of Texas
- R1309
- Created
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2020-04-15Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field