An approach to aminonaphthoquinone ansamycins using a modified Danishefsky diene

Christian A. Kuttruff, Simon Geiger, Mesut Cakmak, Peter Mayer, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

A robust and scalable synthesis of a novel, cyano-substituted Danishefsky-type diene and its use in the Diels-Alder reaction with various dienophiles is reported. The diene allows for the rapid construction of highly substituted aminonaphthoquinones that occur in numerous ansamycin antibiotics.

Original languageEnglish (US)
Pages (from-to)1070-1073
Number of pages4
JournalOrganic Letters
Volume14
Issue number4
DOIs
StatePublished - Feb 17 2012

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Macrocyclic Lactams
Rifabutin
Cycloaddition Reaction
dienes
Anti-Bacterial Agents
Diels-Alder reactions
antibiotics
synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Kuttruff, C. A., Geiger, S., Cakmak, M., Mayer, P., & Trauner, D. (2012). An approach to aminonaphthoquinone ansamycins using a modified Danishefsky diene. Organic Letters, 14(4), 1070-1073. https://doi.org/10.1021/ol203437a

An approach to aminonaphthoquinone ansamycins using a modified Danishefsky diene. / Kuttruff, Christian A.; Geiger, Simon; Cakmak, Mesut; Mayer, Peter; Trauner, Dirk.

In: Organic Letters, Vol. 14, No. 4, 17.02.2012, p. 1070-1073.

Research output: Contribution to journalArticle

Kuttruff, CA, Geiger, S, Cakmak, M, Mayer, P & Trauner, D 2012, 'An approach to aminonaphthoquinone ansamycins using a modified Danishefsky diene', Organic Letters, vol. 14, no. 4, pp. 1070-1073. https://doi.org/10.1021/ol203437a
Kuttruff CA, Geiger S, Cakmak M, Mayer P, Trauner D. An approach to aminonaphthoquinone ansamycins using a modified Danishefsky diene. Organic Letters. 2012 Feb 17;14(4):1070-1073. https://doi.org/10.1021/ol203437a
Kuttruff, Christian A. ; Geiger, Simon ; Cakmak, Mesut ; Mayer, Peter ; Trauner, Dirk. / An approach to aminonaphthoquinone ansamycins using a modified Danishefsky diene. In: Organic Letters. 2012 ; Vol. 14, No. 4. pp. 1070-1073.
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