F. Rudroff et al.
9. Watanabe A, Uchida T, Ito K, Katsuki T (2002) Tetrahedron Lett
43:4481
10. Bolm C, Luong TKK, Schlingloff G (1997) Synlett 1151
11. Mihovilovic MD (2006) Curr Org Chem 10:1265
12. Kamerbeek NM, Janssen DB, van Berkel WJH, Fraaije MW
(2003) Adv Synth Catal 345:667
1H), 5.07–5.27 (m, 2H), 4.42 (m, 1H), 4.00 (m, 1H), 3.21
(m, 1H), 2.65 (m, 1H), 2.36 (m, 1H) ppm; 13C NMR
(50 MHz, CDCl3): d = 176.5, 135.7, 117.4, 72.1, 39.7,
34.1 ppm.
(R)-4-Vinyldihydrofuran-2(3H)-one (Taniguchi lactone)
(11b)
13. Bucko M, Gemeiner P, Schenkmayerova A, Krajcovic T, Rudroff
F, Mihovilovic MD (2016) Appl Microbiol Biotechnol 100:6585
14. Muschiol J, Peters C, Oberleitner N, Mihovilovic MD, Born-
scheuer UT, Rudroff F (2015) Chem Commun 51:5798
15. Rudroff F, Fink MJ, Mihovilovic MD (2016) Miscellaneous key
non-C–C bond forming enzyme reactions. In: Goswami A, Ste-
wart JD (eds) Organic synthesis using biocatalysis. Academic
Press, USA, p 243
16. Leipold F, Rudroff F, Mihovilovic MD, Bornscheuer UT (2013)
Tetrahedron Asymmetry 24:1620
17. Fink MJ, Fischer TC, Rudroff F, Dudek H, Fraaije MW, Miho-
vilovic MD (2011) J Mol Catal B Enzym 73:9
18. Fink MJ, Rudroff F, Mihovilovic MD (2011) Bioorg Med Chem
Lett 21:6135
19. Oberleitner N, Peters C, Muschiol J, Kadow M, Sass S, Bayer T,
Schaaf P, Iqbal N, Rudroff F, Mihovilovic MD, Bornscheuer UT
(2013) ChemCatChem 5:3524
20. Mihovilovic MD, Mu¨ller B, Schulze A, Stanetty P, Kayser MM
(2003) Eur J Org Chem 2243
21. Mihovilovic MD, Rudroff F, Mu¨ller B, Stanetty P (2003) Bioorg
Med Chem Lett 13:1479
An overnight culture with LBkan medium (3 cm3), inocu-
lated with a bacterial single colony from an agar plate and
incubated at 37 °C and 200 rpm in an orbital shaker was
prepared. A baffled Erlenmeyer (500 cm3) flask was
charged with 100 cm3 of LBkan medium and inoculated
with 1% (v/v) of the overnight culture and incubated for
1–2 h under the same conditions until an optical density of
0.2–0.6 was reached. IPTG (0.2 mM) and 50 mg ketone
11a (0.52 mmol, dissolved in 200 mm3 of 1,4-dioxane)
was added. The reaction flask was incubated at 24 °C and
200 rpm in an orbital shaker until full conversion was
determined via GC analysis (18–24 h). After completion of
the reaction, the reaction mixture was centrifuged (12000 x
g, 15 min, 4 °C). The supernatant was extracted with
EtOAc (5 9 40 cm3), and the pooled organic phases were
dried over anhydrous Na2SO4, and concentrated. The
product was purified by column chromatography using
light petroleum and EtOAc. Yields: 57% (33 mg) for
22. Cernuchova P, Mihovilovic MD (2007) Org Biomol Chem
5:1715
23. Fink MJ, Fischer TC, Rudroff F, Dudek H, Fraaije MW, Miho-
vilovic MD (2011) J Mol Catal B Enzym 73:9
24. Fink MJ, Rial DV, Kapitanova P, Lengar A, Rehdorf J, Cheng Q,
Rudroff F, Mihovilovic MD (2012) Adv Synth Catal 354:3491
1
CAMO and 60% (35 mg) for OTEMO. H NMR and 13C
NMR were identical to the racemic Taniguchi lactone [32].
25
[a]D = -7.0 (c = 1 in CHCl3), 99% ee.
¨
25. Mihovilovic MD, Rudroff F, Grotzl B, Kapitan P, Snajdrova R,
Rydz J, Mach R (2005) Angew Chem Int Ed 44:3609
26. Leipold F, Wardenga R, Bornscheuer UT (2012) Appl Microbiol
Biotechnol 94:705
27. Kadow M, Loschinski K, Sass S, Schmidt M, Bornscheuer UT
(2012) Appl Microbiol Biotechnol 96:419
28. Leisch H, Shi R, Grosse S, Morley K, Bergeron H, Cygler M,
Iwaki H, Hasegawa Y, Lau PC (2012) Appl Environ Microbiol
78:2200
29. Kondo K, Mori F (1974) Chem Lett 3:741
30. Lian Jin Liu EK, Hong Joon Hee (2012) Nucleosides Nucleotides
Nucleic Acids 31:411
Acknowledgements Open access funding provided by Austrian
Science Fund (FWF). This work was funded by the Austrian Scien-
tific Foundation FWF (Grant No. I-723-N17). M. J. F. was funded
within the EU-FP7 program Oxygreen (Grant #212281).
Open Access This article is distributed under the terms of the
Creative Commons Attribution 4.0 International License (http://
use, distribution, and reproduction in any medium, provided you give
appropriate credit to the original author(s) and the source, provide a
link to the Creative Commons license, and indicate if changes were
made.
31. Stork G, Niu D, Fujimoto A, Koft ER, Balkovec JM, Tata JR,
Dake GR (2001) J Am Chem Soc 123:3239
32. von Kieseritzky F, Wang Y, Axelson M (2014) Org Process Res
Dev 18:643
33. Ishibashi F, Taniguchi E (1998) Phytochem 49:613
34. Ishibashi F, Taniguchi E (1988) Bull Chem Soc Jpn 61:4361
35. Rial DV, Cernuchova P, van Beilen JB, Mihovilovic MD (2008) J
Mol Catal B Enzym 50:61
References
1. Baeyer A, Villiger V (1899) Chem Berichte 33:124
2. Leisch H, Morley K, Lau PC (2011) Chem Rev 111:4165
3. Mihovilovic MD, Rudroff F, Groetzl B (2004) Curr Org Chem
8:1057
36. Noyori R, Sato T, Kobayashi H (1983) Bull Chem Soc Jpn
56:2661
37. Mihovilovic MD, Kapitan P, Kapitanova P (2008) Chem-
SusChem 1:143
4. Ito K (2012) In: Asymmetric Baeyer-Villiger oxidation. Elsevier
B.V., Amsterdam, p 1
38. Kotkar SP, Suryavanshi GS, Sudalai A (2007) Tetrahedron
Asymmetry 18:1795
5. Michelin RA, Sgarbossa P, Scarso A, Strukul G (2010) Coord
Chem Rev 254:646
6. Sugiishi T, Matsugi M, Hamamoto H, Amii H (2015) RSC Adv
5:17269
7. Uyanik M, Ishihara K (2013) ACS Catal 3:513
8. Xu S, Wang Z, Zhang X, Zhang X, Ding K (2008) Angew Chem
Int Ed 47:2840
¨
39. Ketterer C, Wunsch B (2012) Eur J Org Chem 2012:2428
40. Ketterer C, Grimme S, Weckert E, Wu¨nsch B (2006) Tetrahedron
Asymmetry 17:3046
41. Bode JW, Doyle MP, Protopopova MN, Zhou Q-L (1996) J Org
Chem 61:9146
42. Tanaka M, Mukaiyama C, Mitsuhashi H, Wakamatsu T (1992)
Tetrahedron Lett 33:4165
123