The 17α-hydroxylation of cardiac aglycones. Conversion of the cardenolide to the cortisone side-chain
✍ Scribed by Naftali Danieli; Yehuda Mazur; Franz Sondheimer
- Publisher
- Elsevier Science
- Year
- 1962
- Tongue
- French
- Weight
- 195 KB
- Volume
- 3
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
THE 17a-HYDROXYLATION OF CARDENOLIDES. CONVERSION OF THE CARDENOLIDE TO THE CORTISONE SIDE-CHAIN. N. DANIELI, Y. MAZUR and F. SONDHEIMER. Tetrahedron 23,715 (1967). The [aIn value of 17a-hydroxydigitoxigenin acetate (II) should be -14" @OH) instead of + 155" (EtOH).
## Abstract The 3,6‐di‐__O__‐acetyl derivative 3 of the desulfated aglycone of pectinioside C, (20__S__,24__S__)‐24‐ethylthoransterol A (2), and its 24__R__ and 24__RS__ stereoisomers 4 and 27 have been synthesized stereoselectively from the pregnane derivative 3,6‐di‐__O__‐acetyl‐asterone (5). Her
Five 16α,17α-oxido-steroids were subjected to acids, bases and lithium hydroperoxide. Acids caused Wagner-Meerwein-type rearrangement irrespective of the side-chain structure. The 16α,17α-epoxides proved resistant to bases unless a C( 22)\_O group was present; in the case of 22-esters or 22-ketones