European Journal of Chemistry 2013, 4(3), 191-194 | doi: https://doi.org/10.5155/eurjchem.4.3.191-194.768 | Get rights and content






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A simple stereoselective synthesis of (+)-[6]-gingerdiol


Rathod Aravind Kumar (1) , Jajula Kashanna (2) , Paramesh Jangili (3) , Biswanath Das (4,*)

(1) Organic Chemistry Division-I, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
(2) Organic Chemistry Division-I, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
(3) Organic Chemistry Division-I, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
(4) Organic Chemistry Division-I, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
(*) Corresponding Author

Received: 11 Mar 2013 | Revised: 03 Apr 2013 | Accepted: 12 Apr 2013 | Published: 30 Sep 2013 | Issue Date: September 2013

Abstract


A simple stereoselective synthesis of (+)-[6]-gingerdiol has been accomplished starting from vanillin. The synthetic sequence involves Mouroka allylation, diasterioselective iodine induced electrophilic cyclization and ring-opening of an epoxide as the key steps.

4_3_191_194

Keywords


Vanilline; Gingerdiol; Syn-epoxy alcohol; Maruoka allylation; Electrophilic cyclization; Stereoselective synthesis

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DOI: 10.5155/eurjchem.4.3.191-194.768

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Funding information


Council of Scientific and Industrial Research and University Grants Commission, New Delhi, India

Citations

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[1]. Sachin B. Markad, Viraj A. Bhosale, Suvarna R. Bokale, Suresh B. Waghmode
Stereoselective Approach towards the Synthesis of 3 R , 5  S Gingerdiol and 3  S , 5  S Gingerdiol
ChemistrySelect  4(2), 502, 2019
DOI: 10.1002/slct.201803154
/


References

[1]. Murata, T.; Shinohara, M.; Miyamoto, M. Chem. Pharm. Bull. 1972, 20, 2291-2292.
http://dx.doi.org/10.1248/cpb.20.2291

[2]. Kikuzaki, H.; Tsai, S.-M.; Nakatani, N. Phytochemistry. 1992, 31, 1783-1786.
http://dx.doi.org/10.1016/0031-9422(92)83147-Q

[3]. Sekiva, Y.; Kubota, K.; Kobayashi, A. J. Agric. Food Chem. 2000, 48, 373-377.
http://dx.doi.org/10.1021/jf990674x

[4]. Schuhbaum, H.; Burgermeister, J.; Paper, D. H.; Franz, G. Pharmaceu. Pharmocol. Lett. 2000, 10, 82-85.

[5]. Ficker, C.; Smith, M. L.; Apkagana, K.; Glessor, M.; Zhang, H.; Durst, H.; Assabgui, R.; Arnason, J. T. Phytother Res. 2003, 17, 897-902.
http://dx.doi.org/10.1002/ptr.1335
PMid:13680820

[6]. Franck-Neumann, M.; Geoffroy, P.; Bissinger, P.; Adelaide, S. Tetrahedron Lett. 2001, 42, 6401-6404.
http://dx.doi.org/10.1016/S0040-4039(01)01263-1

[7]. Das, B.; Krishnaiah, M.; Nagendra, S.; Reddy, Ch, R. Lett. Org. Chem. 2011, 8, 244-248.
http://dx.doi.org/10.2174/157017811795371494

[8]. Das, B.; Balasubramanyam, P.; Veeranjaneyulu, B.; Reddy, G. C. Helv. Chem. Acta. 2011, 94, 881-884.
http://dx.doi.org/10.1002/hlca.201000342

[9]. Das, B.; Kumar, D. N. Synlett. 2011, 1285-1287.
http://dx.doi.org/10.1055/s-0030-1260546

[10]. Satyalakshmi, G.; Suneel, K.; Shinde, B. D.; Das, B. Tetrahedron: Asymm. 2011, 22, 1000-1005.
http://dx.doi.org/10.1016/j.tetasy.2011.06.011

[11]. Das, B.; Laxminarayana, K.; Krishnaiah, M.; Kumar, D. N. Helv. Chem. Acta. 2009, 92, 1840-1844.
http://dx.doi.org/10.1002/hlca.200900083

[12]. Nagendra, S.; Krishnaiah, M.; Reddy, K. R.; Das, B. Eur. J. Chem. 2012, 3, 337-339.
http://dx.doi.org/10.5155/eurjchem.3.3.337-339.609

[13]. Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708-1709.
http://dx.doi.org/10.1021/ja020338o
PMid:12580590

[14]. Bartlett, P. A.; Predows, J. D.; Brown, E. G.; Morimoto, A.; Jernstedt, K, K. J. Org. Chem. 1982, 47, 4013-4018.

[15]. Bougini, A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. J. Org. Chem. 1982, 47, 4626-4633.
http://dx.doi.org/10.1021/jo00145a004

[16]. Kumar, P.; Gupta, P.; Naidu, S. V. Chem. Eur. J. 2006, 12, 1397-1402.
http://dx.doi.org/10.1002/chem.200501029
PMid:16308881

How to cite


Kumar, R.; Kashanna, J.; Jangili, P.; Das, B. Eur. J. Chem. 2013, 4(3), 191-194. doi:10.5155/eurjchem.4.3.191-194.768
Kumar, R.; Kashanna, J.; Jangili, P.; Das, B. A simple stereoselective synthesis of (+)-[6]-gingerdiol. Eur. J. Chem. 2013, 4(3), 191-194. doi:10.5155/eurjchem.4.3.191-194.768
Kumar, R., Kashanna, J., Jangili, P., & Das, B. (2013). A simple stereoselective synthesis of (+)-[6]-gingerdiol. European Journal of Chemistry, 4(3), 191-194. doi:10.5155/eurjchem.4.3.191-194.768
Kumar, Rathod, Jajula Kashanna, Paramesh Jangili, & Biswanath Das. "A simple stereoselective synthesis of (+)-[6]-gingerdiol." European Journal of Chemistry [Online], 4.3 (2013): 191-194. Web. 19 Jan. 2020
Kumar, Rathod, Kashanna, Jajula, Jangili, Paramesh, AND Das, Biswanath. "A simple stereoselective synthesis of (+)-[6]-gingerdiol" European Journal of Chemistry [Online], Volume 4 Number 3 (30 September 2013)

DOI Link: https://doi.org/10.5155/eurjchem.4.3.191-194.768

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