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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406819
Subject(s) - cycloaddition , surface modification , chemistry , hydrogen bond , cleavage (geology) , sequence (biology) , combinatorial chemistry , carbon fibers , bond cleavage , photochemistry , stereochemistry , organic chemistry , catalysis , molecule , materials science , biochemistry , fracture (geology) , composite material , composite number
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.