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Synthesis 2004(5): 665-667  
DOI: 10.1055/s-2004-815966
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Kuehneromycin B and Panudial from Kuehneromycin A

Carsten Wallner, Johann Jauch*
Institut für Organische Chemie und Biochemie der Technischen Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany
e-Mail: johann.jauch@ch.tum.de;
Further Information

Publication History

Received 3 September 2003
Publication Date:
10 February 2004 (online)

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Abstract

Syntheses of kuehneromycin B and panudial are presented starting from kuehneromycin A using a thermal decarboxylation under pH control.

Key words

total synthesis - terpenoids - natural products - hydrolysis - decarboxylation

    References

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1

New address: Universität des Saarlandes, Organische Chemie, Postfach 15 11 50, 66041 Saarbrücken, Germany. E-mail: j.jauch@mx-uni-saarland.de.

8

Under the assumption of thermodynamic control DFT calculations (B3LYP/6-31G*) led to ΔΔG(6a/10-epi-6a) of ca. 8 kcal/mol. Thus, the equilibrium constant is ca. 106 in favor of 6a.

9

Unfortunately, the compounds have been mislabeled in the CD spectra shown in Figure [2] a. In the text of ref. [2] the data of the CD spectra have been listed correctly.