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A Unified Strategy for the Syntheses of Angucyclinone Antibiotics: Total Syntheses of Tetrangulol, Kanglemycin M, X-14881-E, and Anhydrolandomycinone

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Title A Unified Strategy for the Syntheses of Angucyclinone Antibiotics: Total Syntheses of Tetrangulol, Kanglemycin M, X-14881-E, and Anhydrolandomycinone
 
Creator VANGA, DG
KALIAPPAN, KP
 
Subject Total synthesis
Synthesis design
Antibiotics
Enynes
Cycloaddition
Metathesis
Aromatization
Photooxygenation
ENANTIOSELECTIVE TOTAL-SYNTHESIS
DIELS-ALDER APPROACH
C-ARYL GLYCOSIDES
(+)-RUBIGINONE B-2
URDAMYCINONE-B
NONAROMATIC ANGUCYCLINONES
RACEMIC VINYLCYCLOHEXENES
AROMATIC ANGUCYCLINONES
STREPTOMYCES SP
RING-SYSTEM
 
Description A unified strategy for the syntheses of angucyclinone antibiotics was developed utilizing sequential intramolecular enyne metathesis, Diels-Alder/aromatization, photooxygenation, and one-pot elimination/aromatization reactions. The diversity in this sequence was introduced in the Diels-Alder reaction where a common diene was treated with various appropriately functionalized quinones as the dienophiles to accomplish the total syntheses of tetrangulol, kanglemycin M, X-14881-E, and anhydrolandomycinone in moderate to good overall yields. The requisite diene was synthesized in excellent yield from a known enyne through an intramolecular enyne metathesis. The scope of this flexible and divergent strategy can be extended to the syntheses of similar scaffolds and unnatural aromatic angucyclinones.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-10-14T13:12:07Z
2014-10-14T13:12:07Z
2012
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (11)2250-2259
http://dx.doi.org/10.1002/ejoc.201200049
http://dspace.library.iitb.ac.in/jspui/handle/100/14489
 
Language en