Total Synthesis of (−)-8-O-Methyltetrangomycin (MM 47755) | Zendy

Christian Kesenheimer | Zendy; Ulrich Groth | Zendy

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Total Synthesis of (−)-8-O-Methyltetrangomycin (MM 47755)

Author(s) -

Christian Kesenheimer,

Ulrich Groth

Publication year - 2006

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol060667b

Subject(s) - chemistry , cycloaddition , anthracene , total synthesis , acetonitrile , stereochemistry , derivative (finance) , natural product , convergent synthesis , geraniol , stereoselectivity , anthraquinone , epoxide , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , chromatography , essential oil , financial economics , economics

A stereoselective total synthesis of the natural antibiotic (-)-8-O-methyltetrangomycin 1 is reported. The essential steps for this convergent synthesis are the transformation of a geraniol epoxide into a chiral octadiyne derivative, which was converted into a triyne. The cobalt-mediated [2+2+2] cycloaddition of the triyne led to a benz[a]anthracene system, which was oxidized with Ag(Py)(2)MnO(4) to a benz[a]anthraquinone. Deprotection with aqueous HF in acetonitrile and photooxidation afforded the desired product (-)-1. [reaction: see text]

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