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Issue 36, 2014
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Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamines

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Abstract

An efficient stereocontrolled preparation of chiral phenanthroindolizidines is detailed. The synthesis relies on the stereoselective indium-mediated allylation of 2-(phenanthren-9-yl)acetaldehyde derivatives with chiral tert-butylsulfinamide. Chemoselective transformations from the corresponding homoallylic sulfinamine allow the synthesis of the phenanthroindolizidines in only three synthetic operations, without any detectable racemization. Following this procedure, the synthesis of natural (−)-tylophorine was successfully accomplished.

Graphical abstract: Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamines

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Publication details

The article was received on 02 Jun 2014, accepted on 16 Jul 2014 and first published on 29 Jul 2014


Article type: Paper
DOI: 10.1039/C4OB01133C
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Citation: Org. Biomol. Chem., 2014,12, 7018-7025
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    Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamines

    C. Anton-Torrecillas and J. C. Gonzalez-Gomez, Org. Biomol. Chem., 2014, 12, 7018
    DOI: 10.1039/C4OB01133C

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