Synthesis of 21-diazoprogesterone-6,7-3H2
✍ Scribed by Wen-Hsiung Chiu; Manfred E. Wolff
- Publisher
- John Wiley and Sons
- Year
- 1979
- Tongue
- French
- Weight
- 354 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
The preparation of 21‐diazoprogesterone‐6,7‐^3^H~2~ is described. Progesterone was dehydrogenated with chloranil to give Δ^6^‐dehydroprogesterone. Degradation of the pregnane side‐chain with sodium hypobromite gave the corresponding carboxylic acid. Catalytic reduction with carrier‐free tritium followed by treatment with oxalyl chloride and then diazomethane afforded 21‐diazoprOgesterone‐6,7‐^3^H~2~ with a specific activity of 42 Ci/mmol.
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## Abstract Syntheses of 5,7‐^3^H~2~ and 4,6‐^3^H~2~ tryptophan, respectively from 2,4,6‐^3^H~3~‐ and 3,5‐^3^H~2~‐aniline, were obtained by Fischer cyclization of suitable labelled phenylhydrazones.
pregnenolone using pregnenolone as s t a r t i n g m a t e r i a l i e described. The procedure involved r e m o v a l of t h e C-21-methyl group of t h e s t e r o i d and t h e side-chain w a s reconstructed with 3H -CH3MgI i n two steps: a Grignard reaction followed by oxidation of t h e resultin