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Angew Chem Int Ed Engl ; 58(50): 18177-18181, 2019 12 09.
Article in English | MEDLINE | ID: mdl-31595605

ABSTRACT

A highly convergent strategy for the synthesis of the natural product (-)-rubriflordilactone B, and the proposed structure of (-)-pseudo-rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium-catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo-rubriflordilactone B and provides a robust platform for further synthetic and biological investigations.


Subject(s)
Triterpenes/chemical synthesis , Alkynes/chemistry , Biological Products/chemistry , Catalysis , Crystallography, X-Ray , Diynes/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Rhodium/chemistry , Stereoisomerism
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