Citation
Dow, William Clinton (1982) Total Synthesis of β-Chamigrene. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/6kmn-mt31. https://resolver.caltech.edu/CaltechTHESIS:05142018-155247666
Abstract
A total synthesis of the sesquiterpene (±)-β-Chamigrene is described. A key step is the preparation of spiroketone ii through Claisen rearrangement of the vinyl-substituted cycloheptapyran i. A modified Meinwald-Cava ring contraction sequence is used for the intramolecular elaboration of a functionalized one-carbon unit at the hindered alpha flank of the spirocycle. This procedure affords ester iii. Alternate reaction pathways available to the reactive ketene intermediate are also discussed. These results are compared with observations made in a previously reported synthesis of aphidicolin.
[Chemical structure included in scanned thesis' abstract, p. iv.]
| Item Type: | Thesis (Dissertation (Ph.D.)) | ||||
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| Subject Keywords: | Chemistry | ||||
| Degree Grantor: | California Institute of Technology | ||||
| Division: | Chemistry and Chemical Engineering | ||||
| Major Option: | Chemistry | ||||
| Thesis Availability: | Public (worldwide access) | ||||
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| Defense Date: | 4 January 1982 | ||||
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| Record Number: | CaltechTHESIS:05142018-155247666 | ||||
| Persistent URL: | https://resolver.caltech.edu/CaltechTHESIS:05142018-155247666 | ||||
| DOI: | 10.7907/6kmn-mt31 | ||||
| Default Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||
| ID Code: | 10882 | ||||
| Collection: | CaltechTHESIS | ||||
| Deposited By: | Mel Ray | ||||
| Deposited On: | 15 May 2018 18:12 | ||||
| Last Modified: | 19 Apr 2021 22:30 |
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