Published June 20, 2014
| Published + Supplemental Material
Journal Article
Open
A Diastereodivergent Synthetic Strategy for the Syntheses of Communesin F and Perophoramidine
Chicago
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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.
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.Attached Files
Published - ol5013263.pdf
Supplemental Material - ol5013263_si_001.pdf
Supplemental Material - ol5013263_si_002.cif
Supplemental Material - ol5013263_si_003.cif
Supplemental Material - ol5013263_si_004.cif
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Additional details
- PMCID
- PMC4068777
- Eprint ID
- 46275
- Resolver ID
- CaltechAUTHORS:20140616-094313057
- NIH
- R01GM080269-01
- Amgen
- Gordon and Betty Moore Foundation
- Caltech
- Fulbright Foundation
- 15111120
- Ilju Foundation of Education & Culture
- Deutscher Akademischer Austauschdienst (DAAD)
- California Tobacco-Related Disease Research Program
- 14FT-0002
- Bristol-Myers Squibb
- Swiss National Science Foundation (SNSF)
- Created
-
2014-06-16Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field