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
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[2]. Sunita Gamre, Mrityunjay Tyagi, Sucheta Chatterjee, Birija S. Patro, Subrata Chattopadhyay, Dibakar Goswami
Synthesis of Bioactive Diarylheptanoids from Alpinia officinarum and Their Mechanism of Action for Anticancer Properties in Breast Cancer Cells
Journal of Natural Products  84(2), 352, 2021
DOI: 10.1021/acs.jnatprod.0c01012
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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. 20 Jan. 2022
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)

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