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Enantioselective Biomimetic Total Syntheses of Kuwanons I and J and Brosimones A and B
Author(s) -
Han Jianguang,
Li Xia,
Guan Yong,
Zhao Wenjun,
Wulff William D.,
Lei Xiaoguang
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404499
Subject(s) - enantioselective synthesis , cycloaddition , chemistry , regioselectivity , intramolecular force , dehydrogenation , tandem , diene , stereochemistry , total synthesis , combinatorial chemistry , organic chemistry , catalysis , materials science , natural rubber , composite material
The first enantioselective total syntheses of prenylflavonoid Diels–Alder natural products (−)‐kuwanon I, (+)‐kuwanon J, (−)‐brosimone A, and (−)‐brosimone B have been accomplished from a common intermediate based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis‐inspired asymmetric Diels–Alder cycloaddition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration to realize a biomimetic dehydrogenation for generation of the required diene precursor. Furthermore, a remarkable tandem inter‐/intramolecular asymmetric Diels–Alder cycloaddition process was applied for the synthesis of (−)‐brosimone A.