<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> / Thesis / Doctor of Philosophy (PhD)
| Identifer | oai:union.ndltd.org:mcmaster.ca/oai:macsphere.mcmaster.ca:11375/18558 |
| Date | 09 1900 |
| Creators | Gravestock, Michael Barry |
| Contributors | Bell, R. A., Chemistry |
| Source Sets | McMaster University |
| Language | English |
| Detected Language | English |
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