Journal of the Chemical Society. Perkin transactions I p. 2745 - 2748 (1990)
Update date:2022-09-26
Topics:
Kirk, David N.
Smith, Carmen Z.
Varley, Michael J.
Honour, John W.
<19-2H3>Progesterone has been prepared from 3,3:20,20-bisethylenedioxy<19-2H3>pregn-5-en-19-ol by reduction of the derived 19-toluene-p-sulphonate with lithium triethylborodeuteride ('superdeuteride') followed by hydrolysis of the ethylenedioxy groups. <18-2H3>Progesterone was obtained from (20R)-3β-acetoxy-pregn-5-eno-20,18-lactone via conversion into methyl (20R)-3β-20-dihydroxypregn-5-en-18-oate: a two-stage introduction of three atoms of deuterium at C-18 via the toluene-p-sulphonate of the derived <18-2H2>-18-ol required unusual experimental conditions.
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Doi:10.1016/S0040-4039(00)97202-2
(1990)Doi:10.1016/S0040-4020(01)90090-0
(1990)Doi:10.1055/s-0030-1260466
(2011)Doi:10.3390/molecules25071610
(2020)Doi:10.1002/anie.201102398
(2011)Doi:10.1021/ol201898x
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