✦ LIBER ✦
The Enantioselective Synthesis of (+)-Estradiol from 1,3-Dihydrobenzo[c]thiophene-2,2-dioxide by Successive Thermal SO2-Extrusion and Cycloaddition Reactions. Preliminary communication
✍ Scribed by Wolfgang Oppolzer; David Anthony Roberts
- Publisher
- John Wiley and Sons
- Year
- 1980
- Tongue
- German
- Weight
- 176 KB
- Volume
- 63
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
The optically pure steroid (+)‐15 has been synthesized from the easily accessible (+)‐carboxylic acid 11 by a sequence of 7 steps in 50% overall yield. The key steps are the regioselective deprotonation/alkylation 7+13 → 14 and the thermal SO~2~‐extrusion/cycloaddition 14 → 15 (Scheme 3). The compound (+)‐15 has been readily converted to the naturally occurring (+)‐estradiol (17) in 60% yield.