Stereocontrolled total synthesis of (+/-)-gelsemine
| dc.contributor.advisor | Fukuyama, Tohru | |
| dc.creator | Liu, Gang | |
| dc.date.accessioned | 2009-06-04T00:19:27Z | |
| dc.date.available | 2009-06-04T00:19:27Z | |
| dc.date.issued | 1996 | |
| dc.description.abstract | Gelsemine (1) has been recognized as the major alkaloid component of Gelsemium sempervirens since 1870. It has attracted numerous synthetic efforts since the 1960s due to its unique rigid, hexacyclic cage structure. The first completely stereocontrolled total synthesis of gelsemine (1) via 21-oxogelsemine (3) is described herein. This synthesis features a stereospecific condensation between cyclopropyl carboxaldehyde (240) and 4-iodo-oxindole (259), facile construction of the tetracyclic intermediate (262) through a novel application of divinylcyclopropane-cycloheptadiene rearrangement, and an unprecedented silver-mediated cyclization between carbamoyl chloride and ene-carbamate.(UNFORMATTED TABLE OR EQUATION FOLLOWS)$$\vbox{\vskip108pt}$$(TABLE/EQUATION ENDS) | |
| dc.format.extent | 222 p. | en_US |
| dc.format.mimetype | application/pdf | |
| dc.identifier.callno | THESIS CHEM. 1996 LIU | |
| dc.identifier.citation | Liu, Gang. "Stereocontrolled total synthesis of (+/-)-gelsemine." (1996) Diss., Rice University. <a href="https://hdl.handle.net/1911/16928">https://hdl.handle.net/1911/16928</a>. | |
| dc.identifier.uri | https://hdl.handle.net/1911/16928 | |
| dc.language.iso | eng | |
| dc.rights | Copyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder. | |
| dc.subject | Organic chemistry | |
| dc.title | Stereocontrolled total synthesis of (+/-)-gelsemine | |
| dc.type | Thesis | |
| dc.type.material | Text | |
| thesis.degree.department | Chemistry | |
| thesis.degree.discipline | Natural Sciences | |
| thesis.degree.grantor | Rice University | |
| thesis.degree.level | Doctoral | |
| thesis.degree.name | Doctor of Philosophy |
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