Synthetic approaches to 19-norsteroids
6β-Acetoxy-3β-benzyloxy-5α-androstan-5-ol-17-one (51), prepared from androstenolone, underwent Westphalen rearrangement to give the 5β-methyl-Δ9(10)-compound. Lead tetraacetate functionalisation of the 5β-methyl group in the 3β-hydroxyl derivative (53) gave 6β-acetoxy-3β,5-oxaethano-19-nor-5β-andros...
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Loughborough University
1973
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ndltd-bl.uk-oai-ethos.bl.uk-4527112019-01-29T03:22:51ZSynthetic approaches to 19-norsteroidsCubberley, Brian W.19736β-Acetoxy-3β-benzyloxy-5α-androstan-5-ol-17-one (51), prepared from androstenolone, underwent Westphalen rearrangement to give the 5β-methyl-Δ9(10)-compound. Lead tetraacetate functionalisation of the 5β-methyl group in the 3β-hydroxyl derivative (53) gave 6β-acetoxy-3β,5-oxaethano-19-nor-5β-androst-9(10)-ene-17-one. Westphalen rearrangement of 6β-cyano-3β-methoxy-5α-cholestan-5-ol (56) cave the 6β-cyano-5β-methyl-derivative (57). Hofmann-Löffler cyclisation of the 6β-N-chloro-N-ethylamino-methyl derivative (62), prepared from this cyano-compound (57), cave none of the anticipated cyclic product (63), but, instead, the products were deduced as being mainly dimeric species (68 and/or 69), in which the 5β-methyl group had probably been functionalised.547.7Loughborough Universityhttps://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.452711https://dspace.lboro.ac.uk/2134/35551Electronic Thesis or Dissertation |
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547.7 |
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547.7 Cubberley, Brian W. Synthetic approaches to 19-norsteroids |
| description |
6β-Acetoxy-3β-benzyloxy-5α-androstan-5-ol-17-one (51), prepared from androstenolone, underwent Westphalen rearrangement to give the 5β-methyl-Δ9(10)-compound. Lead tetraacetate functionalisation of the 5β-methyl group in the 3β-hydroxyl derivative (53) gave 6β-acetoxy-3β,5-oxaethano-19-nor-5β-androst-9(10)-ene-17-one. Westphalen rearrangement of 6β-cyano-3β-methoxy-5α-cholestan-5-ol (56) cave the 6β-cyano-5β-methyl-derivative (57). Hofmann-Löffler cyclisation of the 6β-N-chloro-N-ethylamino-methyl derivative (62), prepared from this cyano-compound (57), cave none of the anticipated cyclic product (63), but, instead, the products were deduced as being mainly dimeric species (68 and/or 69), in which the 5β-methyl group had probably been functionalised. |
| author |
Cubberley, Brian W. |
| author_facet |
Cubberley, Brian W. |
| author_sort |
Cubberley, Brian W. |
| title |
Synthetic approaches to 19-norsteroids |
| title_short |
Synthetic approaches to 19-norsteroids |
| title_full |
Synthetic approaches to 19-norsteroids |
| title_fullStr |
Synthetic approaches to 19-norsteroids |
| title_full_unstemmed |
Synthetic approaches to 19-norsteroids |
| title_sort |
synthetic approaches to 19-norsteroids |
| publisher |
Loughborough University |
| publishDate |
1973 |
| url |
https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.452711 |
| work_keys_str_mv |
AT cubberleybrianw syntheticapproachesto19norsteroids |
| _version_ |
1718968641759739904 |