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A Diastereodivergent Synthetic Strategy for the Syntheses of Communesin F and Perophoramidine

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. http://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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol5013263DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ol5013263PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ol5013263PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4068777/PubMed CentralArticle
ORCID:
AuthorORCID
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
NIHR01GM080269-01
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
Fulbright Foundation15111120
Ilju Foundation of Education & CultureUNSPECIFIED
Deutscher Akademischer Austauschdienst (DAAD)UNSPECIFIED
California Tobacco-Related Disease Research Program14FT-0002
Bristol-Myers SquibbUNSPECIFIED
Swiss National Science Foundation (SNSF)UNSPECIFIED
PubMed Central ID:PMC4068777
Record Number:CaltechAUTHORS:20140616-094313057
Persistent URL:http://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:04 Apr 2019 18:23

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