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Updated: May 24, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
(1S,2R,6R,7aS)-1,2,6-Trihy-droxy-hexa-hydro-1H-pyrrolizin-3-one
Abstract:
In the title compound, C(7)H(11)NO(4), 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 mol-ecules, generating a three-dimensional network. A weak C-H⋯O inter-action also occurs.
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