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

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.

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