Chemoenzymatic Synthesis of
Idesolide from Benzoic Acid

David R. Adams; Christian Aichinger; Jonathan Collins; Uwe Rinner; Tomas Hudlicky

doi:10.1055/s-0030-1259694

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Synlett 2011(5): 725-729
DOI: 10.1055/s-0030-1259694

LETTER

Chemoenzymatic Synthesis of Idesolide from Benzoic Acid

David R. Adams^a, Christian Aichinger^b, Jonathan Collins^a, Uwe Rinner^b, Tomas Hudlicky*^a
^a Chemistry Department and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada
Fax: +1(905)9844841; e-Mail: thudlicky@brocku.ca;
^b Institute of Organic Chemistry, University of Vienna, Währinger Str. 38, 1090 Vienna, Austria

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Publikationsverlauf

Received 20 January 2011
Publikationsdatum:
25. Februar 2011 (online)

Abstract
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Abstract

Idesolide was synthesized in five steps from benzoic acid by base-catalyzed dimerization of hydroxy keto ester, obtained from diol, the product of the whole-cell fermentation of benzoic acid with R. eutrophus B9.

Key words

idesolide - hydroxy keto ester - diol - whole-cell fermentation - benzoic acid

References

1 Kim SH. Sung SH. Choi SY. Chung YK. Kim J. Kim YC. Org. Lett. 2005, 7: 3275

Crossref PubMed Google Scholar
2 Yamakoshi H. Shibuya M. Tomizawa M. Osada Y. Kanoh N. Iwabuchi Y. Org. Lett. 2010, 12: 980

Crossref Google Scholar
3 Nagasawa T. Shimada N. Torihata M. Kuwahara S. Tetrahedron 2010, 66: 4965

Crossref Google Scholar
4 Ekabo OA. Farnsworth NR. Santisuk T. Reutkakul V. J. Nat. Prod. 1993, 56: 699

Crossref Google Scholar
5 Rasmussen B. Nkurunziza A.-J. Witt M. Oketch-Rabah HA. Jaroszewski JW. Sterk D. J. Nat. Prod. 2006, 69: 1300

Crossref Google Scholar
6 Thieme H. Die Pharmazie 1964, 19: 725

Google Scholar
7a Darling SF. Pearl IA. Tetrahedron Lett. 1970, 11: 3827

Google Scholar
7b Darling SF. Pearl IA. Phytochemistry 1971, 10: 3161

Google Scholar
8 Chou C.-J. Lin L.-C. Tsai W.-J. Hsu S.-H. Ho L.-K. J. Nat. Prod. 1997, 60: 375

Crossref Google Scholar
9 Ishikawa T. Nishigaya K. Takami K. Uchikoshi H. Chen I.-S. Tsai I.-L. J. Nat. Prod. 2004, 67: 659

Crossref PubMed Google Scholar
10 Chai XY. Song YL. Xu ZR. Shi HM. Bai CC. Bi D. Wen J. Li FF. Tu PF. J. Nat. Prod. 2008, 71: 814

Crossref Google Scholar
11 Richardson AM. Chen C.-H. Snider BB. J. Org. Chem. 2007, 72: 8099

Crossref Google Scholar
12 Reiner AM. Hegeman GD. Biochemistry 1971, 10: 2530

Crossref PubMed Google Scholar
13 Mihovilovic M. Fischer T. Leisch H. Monatsh. Chem./Chem. Monthly 2010, 141: 699

Google Scholar
14 Damico R. Logan T. J. Org. Chem. 1967, 32: 2356

Crossref Google Scholar
15 Markó IE. Gautier A. Tsukazaki M. Llobet A. Plantalech-Mir E. Urch CJ. Brown SM. Angew. Chem. Int. Ed. 1999, 38: 1960

Crossref Google Scholar
16 Coquerel Y. Brémond P. Rodriguez J. J. Organomet. Chem. 2007, 692: 4805

Crossref Google Scholar
17 Gurjar MK. Yakambram P. Tetrahedron Lett. 2001, 42: 3633

Crossref Google Scholar
18 Myers AG. Siegel DR. Buzard DJ. Charest MG. Org. Lett. 2001, 3: 2923

Crossref PubMed Google Scholar