Synthesis of some cis-fused carbocyclic compounds /
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| Other Authors: | |
| Format: | Thesis Book |
| Language: | English |
| Published: |
[College Station, Tex.] :
May,
1976.
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| Subjects: | |
| Online Access: | Link to OAKTrust copy Link to ProQuest copy |
| Abstract: | The basic goal of this study was the development and utilization of efficient routes for synthesis of some cisfused carbocyclic compounds. The two routes investigated and utilized were the 2 + 2 cycloaddition of cycloalkenes and haloketenes, and the stereospecific cation-initiated intramolecular cyclization of olefinic substrates. The synthesis of bicyclic diols 20 and 21 represent the successful utilization of the 2 + 2 cycloaddition to give the cis-bicyclo[3.2.0]heptane skeleton. Reaction of cyclopentene and dichloroketene gave the dichlorobutanone 23 which was readily converted to ketoacetate 33 by treatment with triethylamine and acetic acid, followed by chromous chloride reduction. Ketoacetate 33 was converted to trans diol 20 by treatment with lithium aluminum hydride. Sequential conversion of ketoacetate 33 into ketol 37 and the corresponding ketosilyl ether 39, followed by reduction with lithium aluminum tri-t-butoxy hydride gave cis diol 21. [Diagram in PDF] The second route to cis-fused bicyclic compounds utilized a stereospecific cationic intramolecular cyclization of the unsaturated ester 81 to the cis-bicyclic ester 80. This cyclization is envisaged to be the key step in the development of stereoselective synthetic approaches to the eremophilane sesquiterpenoid 3-hydroxyeremophilenolide 48c. [Diagram in PDF] |
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| Item Description: | Vita. "Major subject: Chemistry." |
| Physical Description: | xii, 142 leaves ; 28 cm |
| Bibliography: | Includes bibliographical references (leaves 136-141). |