European Journal of Chemistry 2014, 5(1), 127-132 | doi: https://doi.org/10.5155/eurjchem.5.1.127-132.1002 | Get rights and content






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Stereoselective synthesis of (-) Cephalosporolide D


Karna Ji Harkala (1) , Laxminarayana Eppakayala (2,*) , Thirumala Chary Maringanti (3)

(1) Department of Physics and Chemistry, Mahatma Gandhi Institute of Technology, Chaitanya Bharati, Gandipet, Hyderabad-500075, India
(2) Department of Physics and Chemistry, Mahatma Gandhi Institute of Technology, Chaitanya Bharati, Gandipet, Hyderabad-500075, India
(3) Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad College of Engineering, Nachupally, Karimnagar-505501, India
(*) Corresponding Author

Received: 15 Dec 2013 | Revised: 16 Feb 2014 | Accepted: 01 Mar 2014 | Published: 31 Mar 2014 | Issue Date: March 2014

Abstract


A simple and efficient synthesis of eight-membered lactone, Cephalosporolide D has been accomplished from inexpensive and commercially available starting materials. This synthesis utilizes α-aminoxylation catalyzed by L-proline reaction, Jacobsen’s hydrolytic kinetic resolution and Yamaguchi macrolactonization as key steps.


Keywords


α-Aminoxylation; Wittig olefination; Catalytic hydrogenation; Epoxidation with mCPBA; Yamaguchi macrolactonisation; Hydrolytic kinetic resolution of epoxide

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DOI: 10.5155/eurjchem.5.1.127-132.1002

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[1]. Gurrala Alluraiah, Reddymasu Sreenivasulu, Palle Sadanandam, Kowthalam Anitha, Rudraraju Ramesh Raju
A concise stereoselective total synthesis of (−)-cephalosporolide D
Monatshefte für Chemie - Chemical Monthly  147(2), 451, 2016
DOI: 10.1007/s00706-015-1526-4
/


[2]. Mahesh B. Halle, Rodney A. Fernandes
Total Synthesis of Marine Natural Products: Cephalosporolides
Asian Journal of Organic Chemistry  5(7), 839, 2016
DOI: 10.1002/ajoc.201600208
/


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How to cite


Harkala, K.; Eppakayala, L.; Maringanti, T. Eur. J. Chem. 2014, 5(1), 127-132. doi:10.5155/eurjchem.5.1.127-132.1002
Harkala, K.; Eppakayala, L.; Maringanti, T. Stereoselective synthesis of (-) Cephalosporolide D. Eur. J. Chem. 2014, 5(1), 127-132. doi:10.5155/eurjchem.5.1.127-132.1002
Harkala, K., Eppakayala, L., & Maringanti, T. (2014). Stereoselective synthesis of (-) Cephalosporolide D. European Journal of Chemistry, 5(1), 127-132. doi:10.5155/eurjchem.5.1.127-132.1002
Harkala, Karna, Laxminarayana Eppakayala, & Thirumala Chary Maringanti. "Stereoselective synthesis of (-) Cephalosporolide D." European Journal of Chemistry [Online], 5.1 (2014): 127-132. Web. 16 Jul. 2020
Harkala, Karna, Eppakayala, Laxminarayana, AND Maringanti, Thirumala. "Stereoselective synthesis of (-) Cephalosporolide D" European Journal of Chemistry [Online], Volume 5 Number 1 (31 March 2014)

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DOI Link: https://doi.org/10.5155/eurjchem.5.1.127-132.1002

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