A simple biomimetic synthesis of dl-chamaejasmine, a unique 3,3'-biflavanone.
[Reaction: see text] The first chemical synthesis of dl-chamaejasmine (1), a structurally unique 3,3'-biflavanone natural product, was achieved as shown above, by a two-step sequence starting from trimethyl ether derivatives of 3-iodonaringenin (cis + trans) involving (i) metallic lanthanum-mediated reductive dimerization in refluxing THF and (ii) global demethylation with BBr3 in CH2Cl2. This synthesis represents a generally applicable biomimetic (reductive) radical dimerization approach to the 3,3'-biflavonoids.
Li
Wei-Dong Z
WD
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China. liwd@lzu.edu.cn
Ma
Bao-Chun
BC
D044946:Biflavonoids / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics / Q000379:methods; D018360:Crystallography, X-Ray; D044950:Flavanones / Q000138:chemical synthesis* / Q000737:chemistry; D007811:Lanthanum / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
D044946:Biflavonoids; D044950:Flavanones; C511440:chamaejasmine; D007811:Lanthanum; C005273:naringenin