Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B
Literature Information
Publication Date
2015-11-30
DOI
10.1039/C5QO00367A
Impact Factor
5.281
Authors
Emma K. Davison, Jonathan Sperry
View Original
Abstract
In the presence of 1 mol% of a copper(II) catalyst and air, a readily available N1-acetyl-N3-thioacylguanidine undergoes a one-pot benzylic oxidation–oxidative heterocyclization sequence to give the 3-amino-5-acyl-1,2,4-thiadiazole core of polycarpathiamines A (2) and B (3) and thus facilitating the first synthesis of both natural products. This methodology offers a straightforward alternative to the low yielding dipolar cycloaddition used to access 3-amino-5-acyl-1,2,4-thiadiazoles.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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1-(Hexopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl 3-phenylacrylate
CAS Number:
19210-12-9
Molecular Formula:
C24H30O11
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