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- Title
Synthesis of (+)-13-Stemarene and (+)-18-Deoxystemarin: Expeditious Preparation of the Key 6-exo-Hydroxybicyclo2.2.2octan-2-oneEthylene Dithioacetal The numbering refers to the bicyclo2.2.2octane moiety and will be used throughout the text.
- Authors
Francesca Leonelli; Barbara Caschera; Lavinia Silvestri; Alessandro Prastaro; Gaia Corso; Francesca Ceccacci; Angela LaBella; LuisaMaria Migneco; RinaldoMarini Bettolo
- Abstract
An expeditious preparation of the 6-exo-hydroxybicyclo2.2.2octan-2-one ethylene dithioacetal 2b, a key intermediate in the synthesis of (+)-13-stemarene (4) and (+)-18-deoxystemarin (5) is described. Compound 2bwas obtained as the major product by equilibrating the endorich mixture of 6-hydroxybicyclo2.2.2octan-2-one ethylene dithioacetals 2with 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.
- Subjects
ETHYLENE; BENZENE; ORGANIC compounds; KETONES
- Publication
Helvetica Chimica Acta, 2008, Vol 91, Issue 4, p0
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.200890063