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Biomimetic Synthesis: Discovery of Xanthanolide Dimers
Author(s) -
Shang Hai,
Liu Junhua,
Bao Ruiyang,
Cao Yu,
Zhao Kun,
Xiao Chengqian,
Zhou Bing,
Hu Lihong,
Tang Yefeng
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406461
Subject(s) - monomer , chemistry , biomimetic synthesis , head (geology) , combinatorial chemistry , stereochemistry , organic chemistry , biology , polymer , paleontology
Starting from xanthatin, the biomimetic synthesis of 4β,5β‐epoxyxanthatin‐1α,4α‐endoperoxide, a novel monomeric xanthanolide, has been achieved. Moreover, four unprecedented xanthanolide dimers were synthesized by three different dimerizations of xanthatin, either in a head‐to‐head or head‐to‐tail fashion. Notably, these dimeric compounds were firstly identified as artifacts in the laboratory, and two of them, mogolides A and B, proved to be natural products present in the Xanthium mogolium Kitag plant.