Document Detail


Total synthesis of (+)-acutiphycin.
MedLine Citation:
PMID:  17985925     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Synthetic studies toward the total synthesis of (+)-acutiphycin (1) resulted in the discovery of additive-free, highly regioselective nickel-catalyzed reductive coupling reactions of aldehydes and 1,6-enynes and the construction of an advanced intermediate in studies directed toward the synthesis of 1. Ultimately, although not employing the nickel-catalyzed reaction, a highly convergent total synthesis of (+)-acutiphycin featuring an intermolecular SmI2-mediated Reformatsky coupling reaction and macrolactonization initiated by a retro-ene reaction of an alkoxyalkyne was achieved. The resulting synthesis was 18 steps in the longest linear sequence from either methyl acetoacetate or isobutyraldehyde.
Authors:
Ryan M Moslin; Timothy F Jamison
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2007-11-07
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  72     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2007 Dec 
Date Detail:
Created Date:  2007-11-30     Completed Date:  2008-02-20     Revised Date:  2014-09-16    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9736-45     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Crystallography, X-Ray
Heterocyclic Compounds / chemical synthesis*,  chemistry
Macrolides / chemical synthesis*,  chemistry
Models, Molecular
Molecular Structure
Nickel / chemistry
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM-063755/GM/NIGMS NIH HHS; R01 GM063755/GM/NIGMS NIH HHS; R01 GM063755-09/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Heterocyclic Compounds; 0/Macrolides; 0/acutiphycin; 7OV03QG267/Nickel
Comments/Corrections

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