A novel total synthesis of 11-oxygenated steroids
β Scribed by R.P. Stein; G.C. Buzby Jr.; G.H. Douglas; Herchel Smith
- Publisher
- Elsevier Science
- Year
- 1967
- Tongue
- French
- Weight
- 195 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
We wish to report various novel reactions and intermediates which permit the development of efficient total syntheses of a wide variety of 11-oxygenated steroids from intermediates which have previously been converted to estrone, 1,2 equilenin, 1,2 equilin,3 and other steroid hormones.
π SIMILAR VOLUMES
The first total synthesis of 11-tellura steroids was achieved via an intramolecular Diels-Alder cycloaddition of o-quinodimethanes as the key step.
The first total synthesis of 11-oxa steroids was achieved via an intramolecular Diels-Alder cycloaddition of orthoquinodimethane as the key-step.
Conjugate 1,4-addition of 1- [(tert-butyldimethylsilyl)oxy]-2-methyl-1,3-cyclohexadiene (5) to 2-methylcyclopentenone in highly polar media and subsequent alkylation of the resultant silyl enol ether (4) with phenylthiodienyl carbonate I0 in 5.0 M LiC104.Et20 provides substrate 2. Exposure of 2 to T
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