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Steroide. 67. 16,17-Aziridine des Östra-1,3,5(10)-trien-3-methylethers

✍ Scribed by Dr. Brtuno Schönecker; Prof. Dr. Kurt Ponsold

Book ID
105352278
Publisher
John Wiley and Sons
Year
1981
Tongue
English
Weight
480 KB
Volume
323
Category
Article
ISSN
1615-4150

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✦ Synopsis

Steroids. 67. 16,17‐Aziridines of 3‐Methoxy‐estra‐1,3,5(10)‐triene

Reduction of the 16β‐azido‐17‐α‐mesyloxy‐ and 16α‐azido‐17β‐mesyloxy‐estra‐1,3,5(10)‐triene‐3‐methylether (2 and 10) with hydrazine hydrate and Raney nickel gives the 16,17‐trans‐aminoalcohol‐O‐mesylates 3 and 11. Treatment of 3 with basic reagents affords products of Wagner‐Meerwein rearrangement, 11 gives under analogous conditions the 16α‐amino‐17β‐hydroxy compound and the 16α, 17α‐aziridine. Smooth ring closure to the 16,17‐N‐mesylaziridines 6 and 13 can be achieved by reaction of the 16,17‐trans‐mesylamido‐mesyloxy compounds 8 and 12 with bases in DMSO. The torsional angles of the reactive groups are discussed.

📜 SIMILAR VOLUMES

Steroids, XLII. Configurational analysis
Steroids, XLII. Configurational analysis of 3-methoxy-16-methylestra-1,3,5(10)-trien-17-ol derivatives
✍ Meskó, Eszter ;Schneider, Gyula ;Dombi, György ;Zeigan, Dieter 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 English ⚖ 332 KB 👁 1 views

## Abstract The four possible isomers of 16‐hydroxymethyl‐3‐methoxyestra‐1,3,5(10)‐trien‐17‐ol 5a, 6a, 7a, 8a were converted into the corresponding 16‐methyl analogues 4a, 11a, 12a, 13a, which were characterized from their ^1^H‐ and ^13^C‐NMR spectra. The results permit a configurational correlatio