Spiroacetal Formation through Telescoped Cycloaddition and Carbon–Hydrogen Bond Functionalization: Total Synthesis of Bistramide A | Zendy

Han Xun | Zendy; Floreancig Paul E. | Zendy

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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.

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