Publikation:

Total synthesis of (-)-8-O-methyltetrangomycin (MM 47755)

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2006

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Kesenheimer, Christian

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http://nbn-resolving.de/urn:nbn:de:bsz:352-opus-46032
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https://doi.org/10.1021/ol060667b
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Attribution-NonCommercial-NoDerivs 2.0 Generic

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Published

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Organic Letters. 2006, 8(12), pp. 2507-2510. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/ol060667b

Zusammenfassung

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)2MnO4 to a benz[a]anthraquinone. Deprotection with aqueous HF in acetonitrile and photooxidation afforded the desired product (-)-1.

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540 Chemie

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ISO 690KESENHEIMER, Christian, Ulrich GROTH, 2006. Total synthesis of (-)-8-O-methyltetrangomycin (MM 47755). In: Organic Letters. 2006, 8(12), pp. 2507-2510. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/ol060667b
BibTex
@article{Kesenheimer2006Total-9551,
  year={2006},
  doi={10.1021/ol060667b},
  title={Total synthesis of (-)-8-O-methyltetrangomycin (MM 47755)},
  number={12},
  volume={8},
  issn={1523-7060},
  journal={Organic Letters},
  pages={2507--2510},
  author={Kesenheimer, Christian and Groth, Ulrich}
}
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