Enantioselective Synthesis of the Enyne A-Ring Synthon of the 1α-Hydroxy Vitamins D
✍ Scribed by Parker, Kathlyn A.; Dermatakis, Apostolos
- Book ID
- 127354790
- Publisher
- American Chemical Society
- Year
- 1997
- Tongue
- English
- Weight
- 117 KB
- Volume
- 62
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
The vitamin D A-ring synthon, the enyne 3b, was synthesized in 5 steps (37% overall yield) from (S)-(+)-carvone (5). The key step was the SmI2-Pd" mediated transformation of epoxypropargyl ester 6 to 3b.
A diasteroselective carbonyl ene reaction on a substrate obtained from a regioselective propiolate ene reaction is described for the synthesis of 19-norA-ring synthon3.
The asymmetric synthesis of the A-ring of 1α,25-dihydroxyvitamin D 3 , (Z)-2, from 5-tert-butyldimethylsiloxy-2-cyclohexenone [(S)-1], is described where an intramolecular lactonization using cat. scandium triflate is the key reaction.