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 Li,  Ma,  
 

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.[1]

References

  1. A simple biomimetic synthesis of dl-chamaejasmine, a unique 3,3'-biflavanone. Li, W.D., Ma, B.C. Org. Lett. (2005) [Pubmed]
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