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Journal of the American Chemical Society
Architecture by a Divergent Approach: Total Synthesis of (±)-
AUTHOR INFORMATION
Andirolide N via (±)-8α-Hydroxycarapin. J. Am. Chem. Soc.
2017, 139, 631⎯634. (f) Pinkerton, D. M.; Chow, S.; Eisa, N. H.;
Kainth, K.; Vanden Berg, T. J.; Burns, J. M.; Guddat, L. W.;
Savage, G. P.; Chadli, A.; Williams, C. M. Synthesis of the seco-
Limonoid BCD Ring System Identifies a Hsp90 Chaperon
Machinery (p23) Inhibitor. Chem. Eur. J. 2019, 25, 1451-1455.
(5) Schuppe, A. W.; Huang, D.; Chen, Y.; Newhouse, T. R. Total
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Corresponding Author
*E-mail: timothy.newhouse@yale.edu
Author contributions
†A.W.S. and Y. Z. contributed equally to this paper.
ORCID
Synthesis of (−)-Xylogranatopyridine
B via a Palladium-
Catalyzed Oxidative Stannylation of Enones. J. Am. Chem. Soc.
2018, 140, 2062⎯2066.
9
(6) For a review on electrocyclization reactions in biomimetic
synthesis, see: Beaudry, C. M.; Malerich J. P.; Trauner, D.
Biosynthetic and Biomimetic Electrocyclizations. Chem. Rev.
2005, 105, 4757⎯4778.
Timothy R. Newhouse 0000-0001-8741-7236
Alexander W. Schuppe 0000-0001-6002-9110
Yannan Liu 0000-0001-5781-2729
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(7) For select recent examples of 6-electrocyclization sequences in
natural product synthesis, see: (a) Zhang, W.; Ready, J. M. A
Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl
Ynol Ethers as Key Building Blocks. J. Am. Chem. Soc. 2016,
138, 10684⎯10692. (b) Li, H.; Chen, Q.; Lu, Z.; Li, A. Total
Syntheses of Aflavazole and 14-Hydroxyaflavinine. J. Am. Chem.
Soc. 2016, 138, 15555⎯15558. (c) Feng, J.; Lei, X.; Bao, R.; Li,
Y.; Xiao, C.; Hu, L.; Tang, Y. Enantioselective and Collective
Total Syntheses of Xanthanolides. Angew. Chem. Int. Ed. 2017,
56, 16323⎯16327. (d) Murray, L. A.; McKinnie, S. M. K.; Pepper,
H. P.; Erni, R.; Miles, Z. D.; Cruickshank, M. C.; López-Pérez,
B.; Moore, B. S.; George, J. H. Total Synthesis Establishes the
Biosynthetic Pathway to the Naphterpin and Marinone Natural
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Short Synthesis of Delavatine A Unveils New Insights into Site-
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(9) For ketone ,-dehydrogenation, see: (a) Chen, Y.; Huang, D.;
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Funding Sources
Financial support for this work was provided by Yale
University, the Sloan Foundation, Amgen, Bristol-Myers
Squibb (Graduate Fellowship to A.W.S.), the National Science
Foundation (GRFP to A.W.S) and the NIH (GM118614). We
gratefully acknowledge the National Science Foundation for
financial support in the establishment of the Yale University
High Performance Computing (HPC) Center (CNS 08-21132).
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENT
We gratefully acknowledge Dr. Brandon Mercado for X-ray
crystallography of compounds 4, 8, and 14.
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