Enantioselective Total Synthesis of Litseaverticillols A and B

Enantioselective Total Synthesis of Litseaverticillols A and B

The first enantioselective total synthesis of the (1R,5S)-stereoisomer of litseaverticillols A and B, anti-HIV monocyclic sesquiterpenoids isolated from a perennial shrub found in Vietnam, was accomplished in six steps from homogeranic acid by employing the Evans asymmetric aldol reaction and a micr...

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Veröffentlicht in:Organic letters 2006-04, Vol.8 (8), p.1613-1616
Hauptverfasser: Morita, Akira, Kuwahara, Shigefumi
Format: Artikel
Sprache:eng
Schlagworte:
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - chemistry
Anti-HIV Agents - pharmacology
Catalysis
Cyclization
Molecular Structure
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Stereoisomerism
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Zusammenfassung:The first enantioselective total synthesis of the (1R,5S)-stereoisomer of litseaverticillols A and B, anti-HIV monocyclic sesquiterpenoids isolated from a perennial shrub found in Vietnam, was accomplished in six steps from homogeranic acid by employing the Evans asymmetric aldol reaction and a microwave-promoted cyclization of a stannylated thiol ester intermediate as the C−C bond-forming steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol053122a