School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo 669-1337, Japan.
Org Biomol Chem. 2011 Jan 7;9(1):257-64. doi: 10.1039/c0ob00627k. Epub 2010 Nov 17.
The first asymmetric total synthesis of an indole alkaloid, (-)-20-epiuleine, containing the 2,3,4-trisubstituted piperidine core, was achieved using a stereocontrolled one-pot asymmetric 6π-azaelectrocyclization followed by a stereoselective 1,4-addition reaction of the unsaturated ester with a Grignard reagent resulting from the novel neighboring participation of the hydroxyl group in cis-aminoindanol as a chiral nitrogen source.
首次采用立体控制的一锅法不对称 6π-氮杂电环化反应，随后通过不饱和酯与格氏试剂的立体选择性 1,4-加成反应，实现了含 2,3,4-取代哌啶核心的吲哚生物碱 (-)-20-表乌头原碱的不对称全合成，其中格氏试剂由 cis-氨基吲哚醇中羟基的新型邻位参与提供，作为手性氮源。
