Studies Directed toward Asymmetric Synthesis of Cardioactive Steroids via Anionic Polycyclization

Studies Directed toward Asymmetric Synthesis of Cardioactive Steroids via Anionic Polycyclization

The use of anionic polycyclization (AP) in constructing the steroidal backbone of cardenolides was investigated. The reaction of 2-carbomethoxy-2-cyclohexenone I with the enolate of Nazarov reagent II gave, after decarboxylation and aldol condensation, steroid III with control of stereochemistry.

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Veröffentlicht in:Organic letters 2002-12, Vol.4 (26), p.4693-4696
Hauptverfasser: Yang, Zhixiang, Shannon, Dean, Truong, Vouy-Linh, Deslongchamps, Pierre
Format: Artikel
Sprache:eng
Schlagworte:
Cardenolides - chemical synthesis
Cardiotonic Agents - chemical synthesis
Cyclization
Ouabain - chemical synthesis
Stereoisomerism
Steroids - chemical synthesis
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Zusammenfassung:The use of anionic polycyclization (AP) in constructing the steroidal backbone of cardenolides was investigated. The reaction of 2-carbomethoxy-2-cyclohexenone I with the enolate of Nazarov reagent II gave, after decarboxylation and aldol condensation, steroid III with control of stereochemistry.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027125o