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Withsakorn Sangsuwan. Asymmetric synthesis of (+)-epiquinamide from D-Mannose. Master's Degree(Chemistry). Kasetsart University. Office of the University Library. : Kasetsart University, 2017.
Asymmetric synthesis of (+)-epiquinamide from D-Mannose
Name: Withsakorn Sangsuwan
Classification :.LCCS: QD262
LCSH:
Asymmetric synthesis
LCSH:
Heterocyclic compounds
LCSH:
Mannose
Abstract:
(+)-Epiquinamide is a quinolizidine alkaloid isolated from the skin extracts of an Ecuadorian poisonous frog, Epipedobates tricolor. We have successfully synthesized (+)-epiquinamide from D-mannose, an inexpensive and commercially available chiral raw starting material, in 27 steps with overall yield 0.61%. A key step in the synthesis involved reductive ring opening of 2,3-cyclic benzylidene using Cu(OTf)2/BH3.SMe2 to selectively generate 3-OH-2-OBn-α-D-lyxofuranoside. The furanoside ring opening was achieved by the introduction of 5-iodo group followed by Zn-mediated Bernet-Vasella reaction. The bicyclic framework of quinolizidine alkaloid was constructed by ring closing metathesis, Mitsunobu cyclization and intramolecular nucleophilic substitution-cyclization.
Kasetsart University. Office of the University Library
Address:
Bangkok
Email:
tdckulib@ku.ac.th
Name: Boonsong Kongkathip
Role:
Thesis Advisor
Name: Pitak Chuawong
Role:
Thesis Co-Advisor
Created:
2017
Modified:
2023-06-30
Issued:
2023-06-30
วิทยานิพนธ์/Thesis
application/pdf
URL: https://kasetsart.idm.oclc.org/login?url=https://www.lib.ku.ac.th/KUthesis/2560/withsakorn-san-all.pdf
CallNumber:
QD262.W58
eng
DegreeName: Master of Science
Level: Master's Degree
Descipline: Chemistry
Grantor: Kasetsart University
©copyrights Kasetsart University
RightsAccess:
ใช้เวลา
0.033989 วินาที
Withsakorn Sangsuwan
| Title | Contributor | Type |
|---|---|---|
| Asymmetric synthesis of (+)-epiquinamide from D-Mannose
มหาวิทยาลัยเกษตรศาสตร์ Withsakorn Sangsuwan | Boonsong Kongkathip Pitak Chuawong | วิทยานิพนธ์/Thesis |
| Synthesis of 2- and 3-aminonucleoside analogs as inhibitors of asp-tRNAAsn
มหาวิทยาลัยเกษตรศาสตร์ Withsakorn Sangsuwan. | Boonsong Kongkathip. Pitak Chuawong. | วิทยานิพนธ์/Thesis |
Boonsong Kongkathip
Pitak Chuawong