Side-chain truncation of apicularen A by olefin cross-metathesis with ethylene.
The three olefinic double bonds of natural apicularen A (1a) were cleaved by olefin cross-metathesis in the presence of ethylene and Hoveyda-Grubbs catalyst with concomitant E/Z isomerization of Delta(17,18). On extended conversion, 18,19-seco-apicularen A (3) was accumulated and isolated in pure state in 25% yield. In total synthesis, 3 is a valuable late-stage intermediate for side-chain-modified apicularens.
Jundt
Larissa
L
Helmholtz Center for Infection Research (previously GBF, Gesellschaft für Biotechnologische Forschung), Inhoffen Strasse 7, 38124 Braunschweig, Germany.
Höfle
Gerhard
G
D000475:Alkenes / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005030:Ethylenes; C117813:apicularen A; C036216:ethylene