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

Oppolzer Wolfgang | Zendy; Roberts David Anthony | Zendy

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

Author(s) -

Oppolzer Wolfgang,

Roberts David Anthony

Publication year - 1980

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19800630638

Subject(s) - chemistry , cycloaddition , yield (engineering) , regioselectivity , extrusion , deprotonation , enantioselective synthesis , thiophene , alkylation , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , ion , materials science , metallurgy

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.

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