Steroid Total Synthesis, Part II; (?)-17?-Hydroxy-des-A-androst-9-en-5-one
| Autor: | Gabriel Saucy, René Borer |
|---|---|
| Rok vydání: | 1971 |
| Předmět: |
17-Hydroxycorticosteroids
Chemical Phenomena Chemistry Stereochemistry medicine.medical_treatment Organic Chemistry Total synthesis Stereoisomerism Cyclopentanes Ketosteroids Biochemistry Asymmetric induction Catalysis Adduct Steroid Inorganic Chemistry Drug Discovery Methods medicine Amine gas treating Physical and Theoretical Chemistry Enantiomer Androstanes |
| Zdroj: | Helvetica Chimica Acta. 54:2121-2132 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.19710540746 |
| Popis: | Based on the results obtained in the racemic series (part I), (—)-17β-hydroxy-des-A-androst-9-en-5-one has been synthesized, starting with (S)-(—)-5-heptanolide. The key step, viz. the condensation of (S)-(—)-7-hydroxy-1-nonen-3-one (or its amine adduct) with 2-methyl-cyclopentane-1, 3-dione involves an asymmetric induction. Model experiments with (R)-(+)-5-decanolide leading to the enantiomeric homolog of the BCD-tricyclic compound are also described. |
| Databáze: | OpenAIRE |
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