Unexpected Facile Synthesis of Tetronic Acid During the Research on Stereospecific Total Synthesis of (+)-Biotin Starting from D-Erythorbic Acid as Chiral Pool

Xiao-Kang Li; Fei Xiong; Zhong-Yuan Shen; Shu-Ping Zhang; Yi-Hao Zhou; Ming-Lu Xu; Zi-Qian Zhou

doi:10.14233/ajchem.2015.18406

Issue

Vol. 27 No. 5 (2015): Vol 27 Issue 5

Issue Published : February 20, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Unexpected Facile Synthesis of Tetronic Acid During the Research on Stereospecific Total Synthesis of (+)-Biotin Starting from D-Erythorbic Acid as Chiral Pool

https://doi.org/10.14233/ajchem.2015.18406

Xiao-Kang Li

Department of Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China; Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, Jingmen, P.R. China; School of Medical Instrument and Food Engineering, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China

Fei Xiong

Zhong-Yuan Shen

Department of Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China

Shu-Ping Zhang

Department of Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China; School of Medical Instrument and Food Engineering, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China

Yi-Hao Zhou

Department of Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China

Ming-Lu Xu

Department of Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China

Zi-Qian Zhou

Department of Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China

Corresponding Author(s) : Fei Xiong

fxiong@usst.edu.cn; feixiong09@fudan.edu.cn, fduxiong@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 5 (2015): Vol 27 Issue 5
Article Published : February 20, 2015

Abstract

The reaction of D-erythronolactone (8) with the methanesulfonyl chloride in the presence of triethylamine afforded, after unexpected elimination reaction, the tetronic acid is obtained in excellent yield and chemical purity, instead of the dimesylates (7).

Keywords

( )-Biotin D-erythorbic acid Tetronic acid

Li, X.-K., Xiong, F., Shen, Z.-Y., Zhang, S.-P., Zhou, Y.-H., Xu, M.-L., & Zhou, Z.-Q. (2015). Unexpected Facile Synthesis of Tetronic Acid During the Research on Stereospecific Total Synthesis of (+)-Biotin Starting from D-Erythorbic Acid as Chiral Pool. Asian Journal of Chemistry, 27(5), 1957–1958. https://doi.org/10.14233/ajchem.2015.18406

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References

M.A. Boas, Biochem. J., 21, 712 (1927).
M.L. Lazo de la Vega-Monroy, E. Larrieta, M.S. German, A. Baez-Saldana and C. Fernandez-Mejia, J. Nutr. Biochem., 24, 169 (2013); doi:10.1016/j.jnutbio.2012.03.020.
M. Seki, Med. Res. Rev., 26, 434 (2006); doi:10.1002/med.20058.
P.J. De Clercq, Chem. Rev., 97, 1755 (1997); doi:10.1021/cr950073e.
H.F. Dai, W.X. Chen, L. Zhao, F. Xiong, H. Sheng and F.E. Chen, Adv. Synth. Catal., 350, 1635 (2008); doi:10.1002/adsc.200800151.
J. Huang, F. Xiong and F.E. Chen, Tetrahedron Asymm., 19, 1436 (2008); doi:10.1016/j.tetasy.2008.05.020.
F. Xiong, X.X. Chen and F.E. Chen, Tetrahedron Asymm., 21, 665 (2010); doi:10.1016/j.tetasy.2010.03.041.
X.X. Chen, F. Xiong, H. Fu, Z.Q. Liu and F.E. Chen, Chem. Pharm. Bull. (Tokyo), 59, 488 (2011); doi:10.1248/cpb.59.488.
F. Xiong, F.J. Xiong, W.X. Chen, H.Q. Jia and F.E. Chen, J. Heterocycl. Chem., 50, 1078 (2013).
F. Xiong, X.K. Li, M. Xu, S.P. Zhang, F.E. Chen, B. Liao, H.J. Hua and J.H. He, Asian J. Chem., 26, 3659 (2014); doi:10.14233/ajchem.2014.16782.
H.K. Zhang, S.Q. Xu and P.Q. Huang, Pat. CN 101139314, Chem. Abstr., 327110 (2008).
M.G. Scaros, P.K. Yonan, S.A. Laneman and P.N. Fernando, Tetrahedron Asymm., 8, 1501 (1997); doi:10.1016/S0957-4166(97)00156-0.
J. McGarrity and L. Tenud, Eur. Patent Appl. EP273270 A1 (1988); Chem. Abstr., 75168 (1989).
R. Weidenhagen and H. Wegner, Chem. Ber., 72, 2010 (1939); doi:10.1002/cber.19390721122.
F. Micheel and W. Schulte, Justus Liebigs Ann. Chem., 519, 70 (1935); doi:10.1002/jlac.19355190106.

References

M.A. Boas, Biochem. J., 21, 712 (1927).

M.L. Lazo de la Vega-Monroy, E. Larrieta, M.S. German, A. Baez-Saldana and C. Fernandez-Mejia, J. Nutr. Biochem., 24, 169 (2013); doi:10.1016/j.jnutbio.2012.03.020.

M. Seki, Med. Res. Rev., 26, 434 (2006); doi:10.1002/med.20058.

P.J. De Clercq, Chem. Rev., 97, 1755 (1997); doi:10.1021/cr950073e.

H.F. Dai, W.X. Chen, L. Zhao, F. Xiong, H. Sheng and F.E. Chen, Adv. Synth. Catal., 350, 1635 (2008); doi:10.1002/adsc.200800151.

J. Huang, F. Xiong and F.E. Chen, Tetrahedron Asymm., 19, 1436 (2008); doi:10.1016/j.tetasy.2008.05.020.

F. Xiong, X.X. Chen and F.E. Chen, Tetrahedron Asymm., 21, 665 (2010); doi:10.1016/j.tetasy.2010.03.041.

X.X. Chen, F. Xiong, H. Fu, Z.Q. Liu and F.E. Chen, Chem. Pharm. Bull. (Tokyo), 59, 488 (2011); doi:10.1248/cpb.59.488.

F. Xiong, F.J. Xiong, W.X. Chen, H.Q. Jia and F.E. Chen, J. Heterocycl. Chem., 50, 1078 (2013).

F. Xiong, X.K. Li, M. Xu, S.P. Zhang, F.E. Chen, B. Liao, H.J. Hua and J.H. He, Asian J. Chem., 26, 3659 (2014); doi:10.14233/ajchem.2014.16782.

H.K. Zhang, S.Q. Xu and P.Q. Huang, Pat. CN 101139314, Chem. Abstr., 327110 (2008).

M.G. Scaros, P.K. Yonan, S.A. Laneman and P.N. Fernando, Tetrahedron Asymm., 8, 1501 (1997); doi:10.1016/S0957-4166(97)00156-0.

J. McGarrity and L. Tenud, Eur. Patent Appl. EP273270 A1 (1988); Chem. Abstr., 75168 (1989).

R. Weidenhagen and H. Wegner, Chem. Ber., 72, 2010 (1939); doi:10.1002/cber.19390721122.

F. Micheel and W. Schulte, Justus Liebigs Ann. Chem., 519, 70 (1935); doi:10.1002/jlac.19355190106.

Issue

Vol. 27 No. 5 (2015): Vol 27 Issue 5

Unexpected Facile Synthesis of Tetronic Acid During the Research on Stereospecific Total Synthesis of (+)-Biotin Starting from D-Erythorbic Acid as Chiral Pool

Corresponding Author(s) : Fei Xiong

Abstract

Keywords

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