Research Article: (1S,2R,6R,7aS)-1,2,6-Trihy­droxy­hexa­hydro-1H-pyrrolizin-3-one

Date Published: March 01, 2012

Publisher: International Union of Crystallography

Author(s): F. L. Oliveira, K. R. L. Freire, R. Aparicio, F. Coelho.


In the title compound, C7H11NO4, prepared via a Morita–Baylis–Hillman adduct, the five-membered ring bearing three O atoms approximates to a twisted conformation, whereas the other ring is close to an envelope, with a C atom in the flap position. The dihedral angle between their mean planes (all atoms) is 23.11 (9)°. The new stereocenters are created in a trans-diaxial configuration. In the crystal, O—H⋯O and O—H⋯(O,O) hydrogen bonds link the mol­ecules, generating a three-dimensional network. A weak C—H⋯O inter­action also occurs.

Partial Text

For the utilization of this type of pyrrolizidinone as an inihibitor of glicosidase, see: D’Alanzo et al. (2009) ▶; Ayad et al. (2004 ▶) and for their huge therapeutical potential for the treatment of a number of diseases such as cancer, diabetes, and lysosomal storage disorders, see: Baumann (2007 ▶). For related literature concerning preparation of the title compound, see: Freire et al. (2007 ▶). Analysis of the absolute structure was also performed using likelihood methods, see: Hooft et al. (2008 ▶).