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

Carl Johan Wallentin; Edvinas Orentas; Eugenijus Butkus; Kenneth Wärnmark

doi:10.1055/s-0028-1083364

PSP

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

Carl Johan Wallentin^a, Edvinas Orentas^b, Eugenijus Butkus^b, 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;

Abstract

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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%.

Key words

kinetic resolution - bicyclic compounds - synthesis - ketones - chirality

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References

<A NAME="RT14308SS-1">1</A> Butkus E. Synlett 2001, 1827

<A NAME="RT14308SS-2">2</A> Feng S. Xia Y. Han D. Zheng C. He X. Tang X. Bai D. Bioorg. Med. Chem. Lett. 2005, 15: 523

<A NAME="RT14308SS-3">3</A> Usuda H. Kanai M. Shibasaki M. Tetrahedron Lett. 2002, 43: 3621

<A NAME="RT14308SS-4">4</A> Spessard SJ. Stoltz BM. Org. Lett. 2002, 4: 1943

<A NAME="RT14308SS-5">5</A> Otomaru Y. Kina A. Shintani R. Hayashi T. Tetrahedron: Asymmetry 2005, 16: 1673

<A NAME="RT14308SS-6">6</A> Graetz B. Rychnovsky S. Leu W.-H. Farmer P. Lin R. Tetrahedron: Asymmetry 2005, 16: 3584

<A NAME="RT14308SS-7">7</A> Grossman RB. Tsai J.-C. Davis WM. Gutierrez A. Buchwald SL. Organometallics 1994, 13: 3892

<A NAME="RT14308SS-8">8</A> Orentas E. Bagd˛iunas G. Berg U. ilinskas A. Butkus E. Eur. J. Org. Chem. 2007, 4251

<A NAME="RT14308SS-9">9</A> ilinskas A. Stončius S. Butkus E. Chirality 2005, 17: S70

<A NAME="RT14308SS-10">10</A> Butkus E. ilinskas A. Stončius S. Rozenbergas R. Urbanová M. Setnička V. Bour P. Volka K. Tetrahedron: Asymmetry 2002, 13: 633

<A NAME="RT14308SS-11">11</A> Butkus E. Berg U. ilinskas A. Kubilius R. Stončius S. Tetrahedron: Asymmetry 2000, 11: 3053

<A NAME="RT14308SS-12">12</A> Butkus E. Berg U. Malinauskiene J. Sandström J. J. Org. Chem. 2000, 65: 1353

<A NAME="RT14308SS-13">13</A> Naemura K. Matsumura T. Komatsu M. Hirose Y. Chikamatsu H. Bull. Chem. Soc. Jpn. 1989, 62: 3523

<A NAME="RT14308SS-14">14</A> Naemura K. Matsumura T. Komatsu M. Hirose Y. Chikamatsu H. J. Chem. Soc., Chem. Commun. 1988, 239

<A NAME="RT14308SS-15">15</A> Stončius S. Orentas E. Butkus E. Öhrström L. Wendt OF. Wärnmark K. J. Am. Chem. Soc. 2006, 128: 8272

<A NAME="RT14308SS-16">16</A> Stončius S. Butkus E. ilinskas A. Larsson K. Öhrström L. Berg U. Wärnmark K. J. Org. Chem. 2004, 69: 5196

<A NAME="RT14308SS-17">17</A> Marjo C. Bishop R. Eur. J. Org. Chem. 2001, 863

<A NAME="RT14308SS-18">18</A> Butkus E. Berg U. J. Chem. Res., Synop. 1993, 116

<A NAME="RT14308SS-19">19</A> Mitsuo M. Masahiro N. Shigeaki O. Osamu M. Genzoh T. Hiromu K. J. Chem. Technol. Biotechnol. 1998, 281

<A NAME="RT14308SS-20">20</A> Naemura K. Ida H. Fukuda R. Bull. Chem. Soc. Jpn. 1993, 66: 573

<A NAME="RT14308SS-21">21</A> Snatzke G. Wolfram B. Tetrahedron 1972, 28: 655

<A NAME="RT14308SS-22">22</A> Gerlach H. Helv. Chim. Acta 1978, 61: 2773

<A NAME="RT14308SS-23">23</A> Hoffmann G. Wiartalla R. Tetrahedron Lett. 1982, 23: 3887

<A NAME="RT14308SS-24">24</A> Meerwein H. Schurmann W. Justus Liebigs Ann. Chem. 1913, 398: 196

<A NAME="RT14308SS-25">25</A> Schaefer JP. Honig LM. J. Org. Chem. 1968, 33: 2655

<A NAME="RT14308SS-26">26</A> Quast H. Witzel M. Liebigs Ann. Chem. 1993, 699

<A NAME="RT14308SS-27">27</A> Lightner DA. Chang TC. Hefelfinger DT. Jackman DE. Wijekoon WMD. Givens JW. J. Am. Chem. Soc. 1985, 107: 7499

<A NAME="RT14308SS-28">28</A> Mislin G. Miesch M. Eur. J. Org. Chem. 2001, 1753

<A NAME="RT14308SS-29">29</A> Peters JA. Synthesis 1979, 321

<A NAME="RT14308SS-30">30</A> Henkel JG. Faith WC. Hane JT. J. Org. Chem. 1981, 46: 3483

<A NAME="RT14308SS-31">31</A> Mayr M. Bataille CJR. Gosiewska S. Raskatov JA. Brown JM. Tetrahedron: Asymmetry 2008, 19: 1328

<A NAME="RT14308SS-32">32</A> Steven VL. Joanne N. William PG. Stephen PM. Synthesis 1994, 639

Jästbolaget AB, P. O. Box 7003, 192 07 Sollentuna, Sweden.

<A NAME="RT14308SS-34">34</A> Stephens PJ. McCann DM. Butkus E. Stončius S. Cheeseman JR. Frisch MJ. J. Org. Chem. 2004, 69: 1948

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.