Scientific article
German
English

The Enantioselective Synthesis of (+)-Estradiol from 1,3-Dihydrobenzo[c]thiophene-2,2-dioxide by Successive Thermal SO2-Extrusion and Cycloaddition Reactions. Preliminary communication

Published inHelvetica chimica acta, vol. 63, no. 6, p. 1703-1705
Publication date1980-09-17
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 SO2-extrusion/cycloaddition 14 → 15(Scheme 3). The compound (+)-15 has been readily converted to the naturally occurring (+)-estradiol (17) in 60% yield.

Citation (ISO format)
VON OPPOLZER, Wolfgang, ROBERTS, David Anthony. The Enantioselective Synthesis of (+)-Estradiol from 1,3-Dihydrobenzo[c]thiophene-2,2-dioxide by Successive Thermal SO2-Extrusion and Cycloaddition Reactions. Preliminary communication. In: Helvetica chimica acta, 1980, vol. 63, n° 6, p. 1703–1705. doi: 10.1002/hlca.19800630638
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Journal ISSN0018-019X
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