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Evolution of a Unified, Stereodivergent Approach to the Synthesis of Communesin F and Perophoramidine

Han, Seo-Jung and Vogt, Florian and May, Jeremy A. and Krishnan, Shyam and Gatti, Michele and Virgil, Scott C. and Stoltz, Brian M. (2015) Evolution of a Unified, Stereodivergent Approach to the Synthesis of Communesin F and Perophoramidine. Journal of Organic Chemistry, 80 (1). pp. 528-547. ISSN 0022-3263. PMCID PMC4285143. https://resolver.caltech.edu/CaltechAUTHORS:20141202-144818205

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Abstract

Expedient synthetic approaches to the highly functionalized polycyclic alkaloids communesin F and perophoramidine are described using a unified approach featuring a key decarboxylative allylic alkylation to access a crucial and highly congested 3,3-disubstituted oxindole. Described are two distinct, stereoselective alkylations that produce structures in divergent diastereomeric series possessing the critical vicinal all-carbon quaternary centers needed for each synthesis. Synthetic studies toward these challenging core structures have revealed a number of unanticipated modes of reactivity inherent to these complex alkaloid scaffolds. Additionally, several novel and interesting intermediates en route to the target natural products, such as an intriguing propellane hexacyclic oxindole encountered in the communesin F sequence, are disclosed. Indeed, such unanticipated structures may prove to be convenient strategic intermediates in future syntheses.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://pubs.acs.org/doi/abs/10.1021/jo502534gPublisherArticle
http://dx.doi.org/10.1021/jo502534gDOIArticle
http://pubs.acs.org/doi/suppl/10.1021/jo502534gPublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4285143/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: November 5, 2014. Publication Date (Web): November 17, 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) for a postdoctoral fellowship. J.A.M. is grateful for a fellowship by Bristol-Myers Squibb and Amgen. S.K. thanks California TRDRP for financial support (postdoctoral fellowship 14FT-0002). 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. The authors are thankful to Dr. Ryan Zeidan, Dr. Sandy Ma, and Mr. Chung Whan Lee for experimental assistance.
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
Bristol-Myers SquibbUNSPECIFIED
AmgenUNSPECIFIED
California Tobacco-Related Disease Research Program14FT-0002
NSF Postdoctoral FellowshipUNSPECIFIED
Issue or Number:1
PubMed Central ID:PMC4285143
Record Number:CaltechAUTHORS:20141202-144818205
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20141202-144818205
Official Citation:Evolution of a Unified, Stereodivergent Approach to the Synthesis of Communesin F and Perophoramidine Seo-Jung Han, Florian Vogt, Jeremy A. May, Shyam Krishnan, Michele Gatti, Scott C. Virgil, and Brian M. Stoltz The Journal of Organic Chemistry 2015 80 (1), 528-547
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:52292
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:02 Dec 2014 23:22
Last Modified:03 Oct 2019 07:41

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