Total Synthesis of (-)-Allosecurinine

Total Synthesis of (-)-Allosecurinine

Safe and secure: An efficient methodology which provides access to homochiral 2,5‐cis pyrrolidines in excellent yields starting from chiral alkoxyamine cyclopropanes was used in the total synthesis of (−)‐allosecurinine (see scheme). The synthesis proceeds with enantiomeric purity in 15 steps with a...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-09, Vol.47 (41), p.7945-7948
Hauptverfasser: Leduc, Andrew B, Kerr, Michael A
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
Alkaloids - chemical synthesis
asymmetric synthesis
Azepines
Euphorbiaceae - chemistry
heterocycles
Heterocyclic Compounds, Bridged-Ring - chemical synthesis
Lactones
natural products
Piperidines
Pyrrolidines - chemistry
total synthesis
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Zusammenfassung:Safe and secure: An efficient methodology which provides access to homochiral 2,5‐cis pyrrolidines in excellent yields starting from chiral alkoxyamine cyclopropanes was used in the total synthesis of (−)‐allosecurinine (see scheme). The synthesis proceeds with enantiomeric purity in 15 steps with an overall yield of 5 %. OTf: trifluoromethanesulfonate, Boc: tert‐butoxycarbonyl, PG: protecting group.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200803257