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Design and synthesis of ring D modified steroidal hormones
Bibliography: pages 183-190.
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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2016
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| _version_ | 1867613230211268608 |
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| access_status_str | Open Access |
| author | Grundler, Claudia |
| author2 | Bull, James R |
| author_browse | Bull, James R Grundler, Claudia |
| author_facet | Bull, James R Grundler, Claudia |
| author_sort | Grundler, Claudia |
| collection | Thesis |
| description | Bibliography: pages 183-190. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/17372 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:32:50.328Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2016 |
| publishDateRange | 2016 |
| publishDateSort | 2016 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/17372 Design and synthesis of ring D modified steroidal hormones Grundler, Claudia Bull, James R Chemistry Bibliography: pages 183-190. Cycloadditions of steroidal 14,16-dienes with ketene equivalents were investigated, as routes to estradiol and estriol analogues. The cycloadduct of 3-methoxyestra-1,3,5(10), 14,16-pentaen-17-yl acetate and 2-chloroacrylonitrile underwent an unprecedented tandem rearrangement, on attempted alkaline hydrolysis to the corresponding ketone. This product, obtained in ca. 90% yield, was formulated as (16¹R)-3-methoxy-17-oxo-15β,16¹-cyclo-14,16β-ethano-14β-estra-1,3,5(10)-triene-16¹-carbonitrile. The chemistry of the 16¹-carbonitrile was extensively studied and, in addition, the derived estradiol analogues were prepared and evaluated for receptorbinding affinity. The 16¹-carbonitrile, and its derivatives, could be transformed into 14,15-dihydrocyclobutano or 14β,16β-bridged compounds by cleavage of a cyclopropyl bond. Indeed, a 14,15-dihydrocyclobutano estradiol analogue was synthesised and submitted for biological evaluation. The cycloadduct of 3-methoxyestra-1,3,5(10),14,16-pentaen-17-yl acetate and 2-acetoxyacrylonitrile afforded the corresponding 17-hydroxy 16-oxo compound on alkaline hydrolysis. The 17-hydroxy 16-oxo compound was efficiently converted to the 14α,17α-ethano 15,16-etheno compound by the Shapiro reaction. Reduction of the 17- hydroxy 16-oxo compound led to the formation of the corresponding 16,17-diols, which gave the derived 14β-compounds on glycol cleavage. Furthermore, under acidic conditions the 16,17-diols were found to undergo high yield 16(17 --> l7¹)abeo rearrangements, to afford 14,16-etheno compounds. 2016-02-29T12:06:46Z 2016-02-29T12:06:46Z 1992 Doctoral Thesis Doctoral PhD http://hdl.handle.net/11427/17372 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Grundler, Claudia Design and synthesis of ring D modified steroidal hormones |
| thesis_degree_str | Doctoral |
| title | Design and synthesis of ring D modified steroidal hormones |
| title_full | Design and synthesis of ring D modified steroidal hormones |
| title_fullStr | Design and synthesis of ring D modified steroidal hormones |
| title_full_unstemmed | Design and synthesis of ring D modified steroidal hormones |
| title_short | Design and synthesis of ring D modified steroidal hormones |
| title_sort | design and synthesis of ring d modified steroidal hormones |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/17372 |
| work_keys_str_mv | AT grundlerclaudia designandsynthesisofringdmodifiedsteroidalhormones |