Synthesis 2009(5): 864-867  
DOI: 10.1055/s-0028-1083364
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Baker’s Yeast for Sweet Dough Enables Large-Scale Synthesis of Enantiomerically Pure Bicyclo[3.3.1]nonane-2,6-dione

Carl Johan Wallentina, Edvinas Orentasb, Eugenijus Butkusb, Kenneth Wärnmark*a
a Organic Chemistry, Department of Chemistry, Lund University, P.O. Box 124, 22100 Lund, Sweden
Fax: +46(46)2228209; e-Mail: kenneth.warnmark@organic.lu.se;
b Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania
Fax: +370(5)92330987; e-Mail: eugenijus.butkus@chf.vu.lt;
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Publikationsverlauf

Received 22 August 2008
Publikationsdatum:
11. Februar 2009 (online)

Abstract

An improved synthetic procedure of racemic bicyclo[3.3.1]nonane-2,6-dione has been developed. Employing Baker’s yeast for sweet dough made it possible to kinetically resolve the racemic compound and to isolate enantiomerically pure (+)-bicyclo[3.3.1]nonane-2,6-dione on a large scale. Furthermore, the developed procedure made it possible to produce (-)-bicyclo[3.3.1]nonane-2,6-dione with an enantiomeric excess of 75%.

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Ketol 3 can be collected as a nearly 1:1 mixture of the endo- and exo-isomers in the second fraction in the chromato-graphic purification of (+)-1 by eluting with EtOAc.