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Spiroacetal Formation through Telescoped Cycloaddition and Carbon–Hydrogen Bond Functionalization: Total Synthesis of Bistramide A
Author(s) -
Han Xun,
Floreancig Paul E.
Publication year - 2014
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.201406819
Subject(s) - cycloaddition , chemistry , surface modification , total synthesis , hydrogen bond , cleavage (geology) , sequence (biology) , bond cleavage , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , molecule , biochemistry , materials science , fracture (geology) , composite material
Spiroacetals can be formed through a one‐pot sequence of a hetero‐Diels–Alder reaction, an oxidative carbon–hydrogen bond cleavage, and an acid treatment. This convergent approach expedites access to a complex molecular subunit which is present in numerous biologically active structures. The utility of the protocol is demonstrated through its application to a brief synthesis of the actin‐binding cytotoxin bistramide A.