Volume 2014, Issue 3 p. 631-638

Full Paper

Synthesis of GABOB and GABOB-Based Chiral Units Possessing Distinct Protecting Groups

Trpimir Ivšić

[email protected]

Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, 10002 Zagreb, Croatia, http://www.irb.hr/eng/People/Trpimir-Ivsic http://www.irb.hr/eng/Research/Divisions-and-Centers/ Division-of-Organic-Chemistry-and-Biochemistry/Laboratory-for-stereoselective-catalysis-and-biocatalysis

Search for more papers by this author

Irena Dokli,

Irena Dokli

Search for more papers by this author

Ana Rimac,

Ana Rimac

Search for more papers by this author

Zdenko Hameršak,

Zdenko Hameršak

Search for more papers by this author

Trpimir Ivšić,

Trpimir Ivšić

[email protected]

Search for more papers by this author

Irena Dokli,

Irena Dokli

Search for more papers by this author

Ana Rimac,

Ana Rimac

Search for more papers by this author

Zdenko Hameršak,

Zdenko Hameršak

Search for more papers by this author

First published: 25 November 2013

https://doi.org/10.1002/ejoc.201301374

Citations: 5

Share a link

Email
Facebook
Twitter
LinkedIn
Reddit
Wechat

Graphical Abstract

A stereoselective route to GABOB (4-amino-3-hydroxybutanoic acid) derivatives with three different protecting groups is presented. Selective deprotection produced diprotected chiral building blocks with a free carboxylic acid or hydroxy group. Removal of all the protecting groups allowed GABOB to be isolated.

Abstract

In addition to the varied biological activity of GABOB (4-amino-3-hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee.

Supporting Information

References

1 For reviews on this topic, see:
1a M. Ordóñez , V. Labastida-Galván , S. Lagunas-Rivera , Tetrahedron: Asymmetry 2010 , 21 , 129 –147 .
1b M. Ordóñez , C. Cativiela , Tetrahedron: Asymmetry 2007 , 18 , 3 –99 .
2 M. Otsuka , K. Obata , Y. Miyata , Y. Tanaka , J. Neurochem. 1971 , 18 , 287 –295 .
3 E. García-Flores , R. Farías , Stereotactic Functional Neurosurgery 1997 , 69 , 243 –246 .
4 S. Nishiguchi , M. O. Sydnes , A. Taguchi , T. Regnier , T. Kajimoto , M. Node , Y. Yamazaki , F. Yakushiji , Y. Kiso , Y. Hayashi , Tetrahedron 2010 , 66 , 314 –320 .
5 J. Zhu , D. Ma , Angew. Chem. 2003 , 115 , 5506 –5509 ; Angew. Chem. Int. Ed. 2003 , 42 , 5348 –5351 .
6 E. Mete , A. Maraş , H. Seçen , Russ. Chem. Bull. 2003 , 52 , 1879 –1881 .
7 M. E. Jung , T. J. Shaw , J. Am. Chem. Soc. 1980 , 102 , 6304 –6311 .
8 B. Rajashekhar , E. T. Kaiser , J. Org. Chem. 1985 , 50 , 5480 –5484 .
9 J. Häusler , Monatsh. Chem. 1987 , 118 , 865 –869 .
10 M. Tiecco , L. Testaferri , A. Temperini , R. Terlizzi , L. Bagnoli , F. Marini , C. Santi , Synthesis 2005 , 579 –582 .
11 A. Kamal , T. Krishnaji , M. N. A. Khan , J. Mol. Catal. B: Enzym. 2007 , 47 , 1 –5 .
12 A. Kamal , G. B. R. Khanna , T. Krishnaji , R. Ramu , Tetrahedron: Asymmetry 2006 , 17 , 1281 –1289 .
13 A. Nakagawa , H. Idogaki , K. Kato , A. Shinmyo , T. Suzuki , J. Biosci. Bioeng. 2006 , 101 , 97 –103 .
14 R. P. Jain , R. M. Williams , Tetrahedron 2001 , 57 , 6505 –6509 .
15 M. Harding , J. A. Bodkin , F. Issa , C. A. Hutton , A. C. Willis , M. D. McLeod , Tetrahedron 2009 , 65 , 831 –843 .
16 P. D. Theisen , C. H. Heathcock , J. Org. Chem. 1988 , 53 , 2374 –2378 .
17 L. Tamborini , P. Conti , A. Pinto , S. Colleoni , M. Gobbi , C. De Micheli , Tetrahedron 2009 , 65 , 6083 –6089 .
18 K. Iwanami , K. Yano , T. Oriyama , Synthesis 2005 , 2669 –2672 .
19 J. Kato , N. Iwasawa , T. Mukaiyama , Chem. Lett. 1985 , 743 –746 .
20 N. Komatsu , J. Ishida , H. Suzuki , Tetrahedron Lett. 1997 , 38 , 7219 –7222 .
21 J. S. Bajwa , X. Jiang , J. Slade , K. Prasad , O. Repič , T. J. Blacklock , Tetrahedron Lett. 2002 , 43 , 6709 –6713 .
22 K. Iwanami , H. Seo , Y. Tobita , T. Oriyama , Synthesis 2005 , 183 –186 .
23 Y. Bourdreux , A. Lemétais , D. Urban , J.-M. Beau , Chem. Commun. 2011 , 47 , 2146 –2148 .
24 P. Wuts , T. W. Greene , Protective Groups in Organic Synthesis Wiley, Hoboken, N. J., 2006 .
25 M. D. D. de Villegas , J. A. Gálvez , P. Etayo , R. Badorrey , P. López-Ram-de-Víu , Chem. Soc. Rev. 2011 , 40 , 5564 –5587 .
26 Z. Rodriguez-Docampo , S. J. Connon , ChemCatChem 2012 , 4 , 151 –168 .
27 J. T. Starr , G. Koch , E. M. Carreira , J. Am. Chem. Soc. 2000 , 122 , 8793 –8794 .
28 J. Mittendorf , J. Benet-Buchholz , P. Fey , K. H. Mohrs , Synthesis 2003 , 136 –140 .
29 S. P. Keen , C. J. Cowden , B. C. Bishop , K. M. J. Brands , A. J. Davies , U. H. Dolling , D. R. Lieberman , G. W. Stewart , J. Org. Chem. 2005 , 70 , 1771 –1779 .
30 Z. Hameršak , I. Stipetić , A. Avdagić , Tetrahedron: Asymmetry 2007 , 18 , 1481 –1485 .
31 J. Huang , F. Xiong , F. E. Chen , Tetrahedron: Asymmetry 2008 , 19 , 1436 –1443 .
32 L. Ji , Y. Ma , J. Li , L. Zhang , L. Zhang , Tetrahedron Lett. 2009 , 50 , 6166 –6168 .
33 T. Ivšić , Z. Hameršak , Tetrahedron: Asymmetry 2013 , 24 , 217 –222 .
34 C. Bolm , I. Schiffers , C. L. Dinter , A. Gerlach , J. Org. Chem. 2000 , 65 , 6984 –6991 .
35 T. Ivšić , J. Novak , N. Došlić , Z. Hameršak , Tetrahedron 2012 , 68 , 8311 –8317 .
36 T. Ivšić , Z. Hameršak , Tetrahedron: Asymmetry 2009 , 20 , 1095 –1098 .
37 Y. Chen , P. McDaid , L. Deng , Chem. Rev. 2003 , 103 , 2965 –2984 .
38 A. Peschiulli , Y. Gun'k , S. J. Connon , J. Org. Chem. 2008 , 73 , 2454 –2457 .
39 S. E. Park , E. H. Nam , H. B. Jang , J. S. Oh , S. Some , Y. S. Lee , C. E. Song , Adv. Synth. Catal. 2010 , 352 , 2211 –2217 .
40 C. Bolm , I. Schiffers , C. L. Dinter , L. Defrère , A. Gerlach , G. Raabe , Synthesis 2001 , 1719 –1730 .
41 K. Ninomiya , T. Shioiri , S. Yamada , Tetrahedron 1974 , 30 , 2151 –2157 .
42 C. Bolm , I. Schiffers , I. Atodiresei , C. P. R. Hackenberger , Tetrahedron: Asymmetry 2003 , 14 , 3455 –3467 .

Citing Literature

Volume2014, Issue3

January 2014

Pages 631-638

Synthesis of GABOB and GABOB-Based Chiral Units Possessing Distinct Protecting Groups

Graphical Abstract

Abstract

Supporting Information

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Synthesis of GABOB and GABOB-Based Chiral Units Possessing Distinct Protecting Groups

Graphical Abstract

Abstract

Supporting Information

References

Citing Literature

References

Related

Information