Highly stereocontrolled synthesis of natural barbacenic acid, novel bisnorditerpene from Barbacenia flava.
Barbacenic acid, a bisnorditerpene with five contiguous asymmetric centers (four fully substituted), has been prepared for the first time through a highly stereocontrolled route in 5.2% overall yield from a known octalone. The synthesis serves to define the absolute configuration of the natural product.
Patin
Amaury
A
Université Joseph Fourier, LEDSS, BP 53X, 38041 Grenoble Cedex, France.
Kanazawa
Alice
A
Philouze
Christian
C
Greene
Andrew E
AE
Muri
Estela
E
Barreiro
Eliezer
E
Costa
Paulo C C
PC
D002384:Catalysis; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000032:analysis / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D019684:Magnoliopsida / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013020:South America; D013237:Stereoisomerism
D004224:Diterpenes; D007202:Indicators and Reagents; C479498:barbacenic acid