ABSOLUTE CONFIGURATION OF 13-EPIMULINOLIC ACID

作者：Brito Ivan^*; Borquez Jorge; Cardenas Alejandro; Avendano Maria; Simirgiotis Mario

来源：JOURNAL OF THE CHILEAN CHEMICAL SOCIETY, 2017, 62(2): 3535-3537.

DOI：10.4067/s0717-97072017000200022

• Absolute configuration
• Diterpenoid
• X-ray diffraction
• Crystal and Supramolecular structure

The molecular structure of the title compound [iupac name: 13-epi-8-hydroxy-3-isopropyl-5a, 8-dimethyl-2,3,4,5,5a, 6,7,8,10a, 10b-decahydrocyclohepta[e] indene-3a(1H) acid] is similar to the structure of the known compound mulinolic acid. The structure of this mulinolic acid epimer consists of a mulinane skeleton and the isopropyl, methyl group, carboxylic acid and the hydroxyl group at C3, C8, C5, C13, respectively, which are beta-oriented, whereas the methyl group at C13 are a-oriented. The cyclopentane (A), ciclohexane (B) and cicloheptene (C) rings are trans (A/B) and (B/C) cis fused, and are in an envelope, chair, and twist chair conformation respectively. In the crystal the molecules are linked by two strong intermolecular O-H center dot center dot center dot O hydrogen bond forming bidimensional supramolecular structures with graph-set notation (12) and (46). The absolute configuration of the title compound which 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 C13S.

• 出版日期2017-6