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Issue 14, 2005
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Asymmetric syntheses of (−)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate

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Abstract

Ready access to natural (−)-lentiginosine and its pyrrolizidinic analogue from a chiral vinylic epoxyamine in a straightforward five-step sequence is presented. Careful use of the RCM reaction on aminotriols 5 and 6 constitutes the key feature of the synthetic pathway. The α-amyloglucosidase inhibitory activities of the target compounds were evaluated and showed that the more easily accessible pyrrolizidinic analogue possesses an inhibitory activity quite similar to that of (−)-lentiginosine.

Graphical abstract: Asymmetric syntheses of (−)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate

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Publication details

The article was received on 15 Apr 2005, accepted on 17 May 2005 and first published on 13 Jun 2005


Article type: Paper
DOI: 10.1039/B505303J
Org. Biomol. Chem., 2005,3, 2626-2631

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    Asymmetric syntheses of (−)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate

    T. Ayad, Y. Génisson and M. Baltas, Org. Biomol. Chem., 2005, 3, 2626
    DOI: 10.1039/B505303J

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