Document Detail


A Concise Total Synthesis of (+)-Scholarisine A Empowered by a Unique C-H Arylation.
MedLine Citation:
PMID:  23964983     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C-H arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels-Alder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule's quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone.
Authors:
Myles W Smith; Scott A Snyder
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-8-21
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  -     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2013 Aug 
Date Detail:
Created Date:  2013-8-22     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Chemistry, Columbia University , Havemeyer Hall, 3000 Broadway, New York, New York 10027, United States.
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