Use this URL to cite or link to this record in EThOS: | https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.253943 |
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Title: | Approaches to the synthesis of steroidal α-methylene lactones | ||||||
Author: | Chagonda, Lameck S. |
ISNI:
0000 0001 3525 9088
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Awarding Body: | Loughborough University of Technology | ||||||
Current Institution: | Loughborough University | ||||||
Date of Award: | 1982 | ||||||
Availability of Full Text: |
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Abstract: | |||||||
A brief review of the biological properties and the synthesis of α-methylene-γ- and -δ-lactones is presented. Estrone 69 was converted to estrololactone-methyl ether 71 which was α-formylated with ethyl formate, diethylaminated, hydrogenated and underwent β-elimination to the 3-methoxy-16-methylene-17-oxa-17a-oxa-D-homo-estra-1,3,5(10)-triene 75 which was reduced to the 16-methyl lactone 77 and thiolated to the thiol-adduct 76. The estrololactone 70a was α-formylated, acetylated, diethylaminated, hydrogenated and underwent β-elimination to the 3-acetoxy-16-methylene-17-oxo-17a-oxa-D-homo-estra-1,3,5(10)-triene 99 which was hydrolysed to the 3-hydroxy-16-methylene lactone 78. The reaction of the estrololactone methyl ether 71 with triphenylphosphonium ethyl bromide gave 3-methoxy-16-isopropylidene-17-oxo-17a-oxa-D-homo-estro-1,3,5(10)-triene 100.
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Supervisor: | Not available | Sponsor: | Loughborough University of Technology ; British Council | ||||
Qualification Name: | Thesis (Ph.D.) | Qualification Level: | Doctoral | ||||
EThOS ID: | uk.bl.ethos.253943 | DOI: | Not available | ||||
Keywords: | Organic chemistry | ||||||
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