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Synthesis 2004(5): 665-667
DOI: 10.1055/s-2004-815966
DOI: 10.1055/s-2004-815966
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Kuehneromycin B and Panudial from Kuehneromycin A
Weitere Informationen
Received
3 September 2003
Publikationsdatum:
10. Februar 2004 (online)
Publikationsverlauf
Publikationsdatum:
10. Februar 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
- 2
Erkel G.Lorenzen K.Anke T.Velten R.Gimenez A.Steglich W. Z. Naturforsch. C: Biosci. 1995, 50: 1 - 3
Jauch J. Angew. Chem. Int. Ed. 2000, 39: 2764 ; Angew. Chem. 2000, 112, 2874 - 4
Lorenzen K.Anke T.Anders U.Hindermayr H.Hansske F. Z. Naturforsch. C: Biosci. 1994, 49: 132 - 5
Jauch J.Wallner C.Herdtweck E. Eur. J. Org. Chem. 2003, 3060 - 6 See e.g.:
March J. Advanced Organic Chemistry 4th ed.: Wiley; New York: 1992. p.629 ; and literature cited therein - 7 See e.g.:
March J. Advanced Organic Chemistry 4th ed.: Wiley; New York: 1992. p.631 - 10 CRC Handbook of Chemistry and Physics 82nd ed.: Chapman & Hall/CRC; New York: 2001.
References
New address: Universität des Saarlandes, Organische Chemie, Postfach 15 11 50, 66041 Saarbrücken, Germany. E-mail: j.jauch@mx-uni-saarland.de.
8Under 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.
9Unfortunately, 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.