Synthesis and Reactivity of (+)-16-Deoxo-15-oxoisosteviol

Martin Bomkamp; Katharina Gottfried; Olga Kataeva; Siegfried R. Waldvogel

doi:10.1055/s-2008-1072533

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Synthesis 2008(9): 1443-1447
DOI: 10.1055/s-2008-1072533

PAPER

Synthesis and Reactivity of (+)-16-Deoxo-15-oxoisosteviol

Martin Bomkamp^a, Katharina Gottfried^a, Olga Kataeva^b, Siegfried R. Waldvogel*^a
^a Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
^b A.E. Arbuzov Institute of the Russian Academy of Sciences, Arbuzov Street 8, Kazan 420088, Russian Federation
Fax: +49(228)739608; e-Mail: waldvogel@uni-bonn.de;

Further Information

Publication History

Received 26 November 2007
Publication Date:
27 March 2008 (online)

Abstract
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Abstract

The synthesis of optically pure (-)-isosteviol derivatives with a keto function shifted to position 15 and its insertive esterification are described.

Key words

terpenoids - chiral pool - esters - carbocycles - rearrangements

References

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14

Tested reaction conditions for the synthesis of 8: (+)-Methyl-ent-15-oxobeyeran-19-oate (6) was dissolved in toluene, chlorobenzene or 1,2-dichlorobenzene and, after addition of catechol and a catalytic amount of a Brønsted acid, the mixture was heated under reflux applying a Dean-Stark trap. Even under very harsh conditions such as TsOH in boiling 1,2-dichlorobenzene (180 °C) or TfOH in boiling toluene, no product formation was observed.

21

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