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A simple biomimetic synthesis of dl-chamaejasmine, a unique 3,3'-biflavanone.

Authors
Type
Published Article
Journal
Organic Letters
1523-7052
Publisher
American Chemical Society
Publication Date
Volume
7
Issue
2
Pages
271–274
Identifiers
PMID: 15646975
Source
Medline
License
Unknown

Abstract

[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.

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