Total synthesis of the proposed structure of trichodermatide A

Eddie Myers, Elena Herrero-Gómez, Irina Albrecht, Jennifer Lachs, Peter Mayer, Matti Hanni, Christian Ochsenfeld, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

A short total synthesis of the published structure of racemic trichodermatide A is reported. Our synthesis involves a Knoevenagel condensation/Michael addition sequence, followed by the formation of tricyclic hexahydroxanthene-dione and a diastereoselective bis-hydroxylation. The final product, the structure of which was confirmed by X-ray crystallography, has NMR spectra that are very similar, but not identical, to those of the isolated natural product. Quantum chemically computed 13C shifts agree well with the present NMR measurements. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)9812-9817
Number of pages6
JournalJournal of Organic Chemistry
Volume79
Issue number20
DOIs
StatePublished - Oct 17 2014

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Nuclear magnetic resonance
Hydroxylation
X ray crystallography
Biological Products
Condensation
trichodermatide A

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Myers, E., Herrero-Gómez, E., Albrecht, I., Lachs, J., Mayer, P., Hanni, M., ... Trauner, D. (2014). Total synthesis of the proposed structure of trichodermatide A. Journal of Organic Chemistry, 79(20), 9812-9817. https://doi.org/10.1021/jo501206k

Total synthesis of the proposed structure of trichodermatide A. / Myers, Eddie; Herrero-Gómez, Elena; Albrecht, Irina; Lachs, Jennifer; Mayer, Peter; Hanni, Matti; Ochsenfeld, Christian; Trauner, Dirk.

In: Journal of Organic Chemistry, Vol. 79, No. 20, 17.10.2014, p. 9812-9817.

Research output: Contribution to journalArticle

Myers, E, Herrero-Gómez, E, Albrecht, I, Lachs, J, Mayer, P, Hanni, M, Ochsenfeld, C & Trauner, D 2014, 'Total synthesis of the proposed structure of trichodermatide A', Journal of Organic Chemistry, vol. 79, no. 20, pp. 9812-9817. https://doi.org/10.1021/jo501206k
Myers E, Herrero-Gómez E, Albrecht I, Lachs J, Mayer P, Hanni M et al. Total synthesis of the proposed structure of trichodermatide A. Journal of Organic Chemistry. 2014 Oct 17;79(20):9812-9817. https://doi.org/10.1021/jo501206k
Myers, Eddie ; Herrero-Gómez, Elena ; Albrecht, Irina ; Lachs, Jennifer ; Mayer, Peter ; Hanni, Matti ; Ochsenfeld, Christian ; Trauner, Dirk. / Total synthesis of the proposed structure of trichodermatide A. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 20. pp. 9812-9817.
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