JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 62 No 3 (2017): Journal of the Chilean Chemical Society
Original Research Papers

ABSOLUTE CONFIGURATION OF MULINOLIC ACID

Iván Brito
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Jorge Borquez
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Emily Huarote
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Luis Loyola
Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta
Alejandro Cárdenas
Departamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta
Mario Simirgiotis
Instituto de Farmacia, Facultad de Ciencias, Universidad Austral de Chile
Published September 2, 2017
Keywords
  • absolute configuration,
  • diterpenoid,
  • X-ray diffraction,
  • crystal and supramolecular structure

Abstract

The structure of this mulinolic acid consists of a mulinane skeleton and the corresponding isopropyl, methyl, carboxyl and methyl groups at C3, C8, C5, C13, respectively, which are β-oriented, whereas the hydroxyl group at C13 is α-oriented. The cyclopentane (A), ciclohexane (B) and cicloheptene (C) rings are trans (A/B) and (B/C) cis fused, and in an envelope, chair, and twist conformation respectively.

In the crystal the molecules are linked by two intermolecular O-H⋅⋅⋅O hydrogen bond forming bidimensional supramolecular structures with graph-set notation R44(12), R44(40), R66(46) and C44(46). The absolute configuration of the title compound has been determined from the refinement of the Flack parameter16. On this basis the absolute configuration was assigned as C3R, C5S, C8S, C9S, C10S and C13R.

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