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

Kesenheimer, Christian; Groth, Ulrich

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

Dateien

Total_synthesis_of_8O.pdfGröße: 116.1 KBDownloads: 559

Datum

2006

Autor:innen

Kesenheimer, Christian

Groth, Ulrich

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

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.

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

KESENHEIMER, 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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