American Chemical Society
ol047718u_si_002.pdf (1.44 MB)

A Simple Biomimetic Synthesis of dl-Chamaejasmine, a Unique 3,3‘-Biflavanone

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journal contribution
posted on 2005-01-20, 00:00 authored by Wei-Dong Z. Li, Bao-Chun Ma
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.