Absolute configuration of 18-acetoxy-cis-cleroda-3,13e-dien-15-oic acid

• Autores: Iván Brito, Jorge Borquez Ramirez, Diego Robledo, Mario Juan Simirgiotis, Alejandro Cárdenas
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 63, Nº. 3, 2018, págs. 4086-4089
• Idioma: inglés
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• Resumen

  • In this paper we report the absolute configuration which has been determined from the refinement of the Flack parameter, x = 0.05(5), which indicate that the correct configuration had been assigned against 1353 (99%) CuKα Bijvoet pairs. On this basis the absolute configuration was assigned as C5R, C8S, C9R and C10S. The structure of 18-acetoxy-cis-cleroda-3,13E-dien-15-oic acid consists of a clerodane skeleton and the corresponding methyl groups are α-oriented (C8, C9) while C5 is β-oriented. The acidic lateral chain is β-oriented and the double bond between C13 and C14 has E isomeric. The ciclohexene, cyclohexane rings are cis fused, and in an sofa and chair conformation respectively. In the crystal the molecules are linked by one intermolecular O—H…O hydrogen bond forming 1D-dimensional chain with distance donor-acceptor of 2.060(6)Å with graph-set notation C 1 1(15).