Han, Seo-Jung and Vogt, Florian and Krishnan, Shyam and May, Jeremy A. and Gatti, Michele and Virgil, Scott C. and Stoltz, Brian M. (2014) A Diastereodivergent Synthetic Strategy for the Syntheses of Communesin F and Perophoramidine. Organic Letters, 16 (12). pp. 3316-3319. ISSN 1523-7060. PMCID PMC4068777. doi:10.1021/ol5013263. https://resolver.caltech.edu/CaltechAUTHORS:20140616-094313057
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Abstract
An efficient, unified, and stereodivergent approach toward communesin F and perophoramidine was examined. The C(3) all-carbon quaternary center of an oxindole was smoothly constructed by base-promoted indolone-malonate alkylation chemistry. The complementary relative stereochemistry of the crucial vicinal quaternary centers found in communesin F and perophoramidine was selectively installed by substrate-controlled decarboxylative allylic alkylations.
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| Additional Information: | © 2014 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Received: May 8, 2014. Publication Date (Web): June 9, 2014. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. S.-J.H. thanks Fulbright (Foreign Student Program, No. 15111120) and the Ilju Foundation of Education & Culture (Predoctoral Research Fellowship) for financial support. F.V. thanks the German Academic Exchange Service (DAAD) (postdoctoral fellowship). S.K. thanks California TRDRP for financial support (postdoctoral fellowship 14FT- 0002). J.A.M. is grateful for a fellowship by Bristol-Myers Squibb and Amgen. M.G. is grateful to the Swiss National Science Foundation for financial support (postdoctoral fellowship). Dr. David VanderVelde (Caltech) is gratefully acknowledged for assistance with the characterization of compounds by NMR spectroscopy. Lawrence Henling (Caltech) is acknowledged for X-ray crystallographic structural determination. | ||||||||||||||||||||||
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| Issue or Number: | 12 | ||||||||||||||||||||||
| PubMed Central ID: | PMC4068777 | ||||||||||||||||||||||
| DOI: | 10.1021/ol5013263 | ||||||||||||||||||||||
| Record Number: | CaltechAUTHORS:20140616-094313057 | ||||||||||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20140616-094313057 | ||||||||||||||||||||||
| Official Citation: | A Diastereodivergent Synthetic Strategy for the Syntheses of Communesin F and Perophoramidine Seo-Jung Han, Florian Vogt, Shyam Krishnan, Jeremy A. May, Michele Gatti, Scott C. Virgil, and Brian M. Stoltz Organic Letters 2014 16 (12), 3316-3319 | ||||||||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||||||||
| ID Code: | 46275 | ||||||||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||||||||||||
| Deposited On: | 16 Jun 2014 19:59 | ||||||||||||||||||||||
| Last Modified: | 10 Nov 2021 17:23 |
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