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http://hdl.handle.net/11375/18558
Title: | Synthesis of Labdane Diterpenoids |
Authors: | Gravestock, Michael Barry |
Advisor: | Bell, R. A. |
Department: | Chemistry |
Keywords: | chemistry;synthesis;labdane diterpenoid |
Publication Date: | Sep-1969 |
Abstract: | <p> The previously known, 8-oxo-(13→17)-pentanorlabda-12,19-dioic acid 19-methyl ester 36, was synthesised via two routes following the extensive investigation of the dehydrobromination of bromo-ketone 48, and also partial ozonolysis of the phenolic ring of podocarpic acid. </p> <p> This keto-acid 36 has been transformed to the corresponding 8-methylene compound in high yield. Application of the latter intermediate to diterpene synthesis has been demonstrated by the synthesis of 12-hydroxylabd-8(17)-en-19-oic acid 37 and methyl 12-ketolambertianate 61. </p> <p> During investigation of other synthetic intermediates a selective reducing agent for carboxylic esters in the presence of the carboxylic acid function - sodium trimethoxyborohydride, has been discovered. </p> |
URI: | http://hdl.handle.net/11375/18558 |
Appears in Collections: | Open Access Dissertations and Theses |
Files in This Item:
File | Description | Size | Format | |
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Gravestock_Michael_B_1969Sept_PhD.pdf | 50.25 MB | Adobe PDF | View/Open |
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