Dissemin is shutting down on January 1st, 2025

Published in

Wiley, Helvetica Chimica Acta, 4(91), p. 598-607, 2008

DOI: 10.1002/hlca.200890063

Links

Tools

Export citation

Search in Google Scholar

Synthesis of (+)-13-Stemarene and (+)-18-Deoxystemarin: Expeditious Preparation of the Key 6-exo-Hydroxybicyclo[2.2.2]octan-2-one Ethylene Dithioacetal

This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

Full text: Unavailable

Green circle
Preprint: archiving allowed
Orange circle
Postprint: archiving restricted
Red circle
Published version: archiving forbidden
Data provided by SHERPA/RoMEO

Abstract

An expeditious preparation of the 6-exo-hydroxybicyclo[2.2.2]octan-2-one ethylene dithioacetal 2b, a key intermediate in the synthesis of (+)-13-stemarene (4) and (+)-18-deoxystemarin (5) is described. Compound 2b was obtained as the major product by equilibrating the endo rich mixture of 6-hydroxybicyclo[2.2.2]octan-2-one ethylene dithioacetals 2 with TsOH in benzene at reflux, easily available from the corresponding hydroxy ketones 9. The model experiments which preceeded the above transformation, not previously described in the literature, are also presented.