Reimann, Christopher E. and Ngamnithiporn, Aurapat and Hayashida, Kohei and Saito, Daisuke and Korch, Katerina M. and Stoltz, Brian M. (2021) The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′-epi-Leucophyllidine. Angewandte Chemie International Edition, 60 (33). pp. 17957-17962. ISSN 1433-7851. PMCID PMC8338904. doi:10.1002/anie.202106184. https://resolver.caltech.edu/CaltechAUTHORS:20210527-093457752
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Abstract
A synthetic approach to the heterodimeric bisindole alkaloid leucophyllidine is disclosed herein. An enantioenriched lactam building block, synthesized through palladium-catalyzed asymmetric allylic alkylation, served as the precursor to both hemispheres. The eburnamonine-derived fragment was synthesized through a Bischler–Napieralski/hydrogenation approach, while the eucophylline-derived fragment was synthesized by Friedländer quinoline synthesis and two sequential C−H functionalization steps. A convergent Stille coupling and phenol-directed hydrogenation united the two monomeric fragments to afford 16′-epi-leucophyllidine in 21 steps from commercial material.
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| Additional Information: | © 2021 Wiley-VCH. Issue Online: 03 August 2021; Version of Record online: 06 July 2021; Accepted manuscript online: 25 May 2021; Manuscript received: 07 May 2021. We thank the NIH-NIGMS (R01GM080269) for financial support. Portions of this research were also funded by the NSF under the CCI Center for Selective C−H functionalization (CCHF) CHE-1700982. A.N. thanks the Royal Thai Government Scholarship Program. D.S. and K.H. thank Nippon Chemiphar for funding. We thank Dr. David VanderVelde (Caltech) for NMR expertise, Dr. Scott Virgil (Caltech) for instrumentation and analytical support, Dr. Michael Takase and Larry Henling (Caltech) for assistance with X-ray analysis, and Dr. Mona Shahgholi and Naseem Torian (Caltech) for mass spectroscopy. Professor Toh-Seok Kam (U. of Malaya) is acknowledged for providing a sample of leucophyllidine for direct analytical comparison. The authors declare no conflict of interest. | ||||||||||
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| Subject Keywords: | alkaloids; convergence; cross-coupling; divergence; total synthesis | ||||||||||
| Issue or Number: | 33 | ||||||||||
| PubMed Central ID: | PMC8338904 | ||||||||||
| DOI: | 10.1002/anie.202106184 | ||||||||||
| Record Number: | CaltechAUTHORS:20210527-093457752 | ||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20210527-093457752 | ||||||||||
| Official Citation: | The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′-epi-Leucophyllidine. C. E. Reimann, A. Ngamnithiporn, K. Hayashida, D. Saito, K. M. Korch, B. M. Stoltz, Angew. Chem. Int. Ed. 2021, 60, 17957; DOI: 10.1002/anie.202106184 | ||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||
| ID Code: | 109281 | ||||||||||
| Collection: | CaltechAUTHORS | ||||||||||
| Deposited By: | George Porter | ||||||||||
| Deposited On: | 27 May 2021 17:10 | ||||||||||
| Last Modified: | 17 Aug 2022 16:36 |
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