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Construction of Two Vicinal Quaternary Carbons by Asymmetric Allylic Alkylation: Total Synthesis of Hyperolactone C and (−)‐Biyouyanagin A
Author(s) -
Du Chao,
Li Liqi,
Li Ying,
Xie Zhixiang
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200902908
Subject(s) - vicinal , tsuji–trost reaction , alkylation , yield (engineering) , total synthesis , allylic rearrangement , enantiomer , palladium , chemistry , stereochemistry , catalysis , medicinal chemistry , organic chemistry , materials science , metallurgy
Call on triple A : Palladium‐catalyzed asymmetric allylic alkylation (Pd‐AAA; see scheme) has enabled a concise and efficient synthesis of hyperolactone C and (−)‐biyouyanagin A in only six (20 % overall yield) and seven (8 % overall yield) steps, respectively. The enantiomers of these natural products were also prepared by exploiting the same methodology.