Carbon-13 NMR study of (20,24)-epoxydammarane triterpenes

Assignments of the 13C NMR signals of the dammarane triterpenes, 3B,25,30-trihydroxy-(20R,24R)-epoxy-dammaran-16-one 3,30-diacetate (trevoagenin A diacetate) (2), its 20S-isomer (trevoagenin B diacetate) (3) and their related (20R)-3B,30-diacetoxy-16-oxo-25,26,27-trisnordammarane-24,20-lactone (4) and its 20Sisomer (5) have been achieved. Suitable tetrahydrofuran models have been synthesized in order to aid the 13C NMR assignments of the side-chain carbons of the above-mentioned compounds. The remakable chemical shift differences observed for C-21 and C-22 between each pair of the C-20 epimers (2, 3 and 4, 5) allowed the confirmation of the C-20 stereochemistry of these ocotillo-type dammarane triterpenes.

Bibliographic Details

Main Authors:	Francisco, Cosme G., Freire, Raimundo, Hernández, Rosendo, Salazar, José A., Suárez, Ernesto, Cortés, Manuel
Other Authors:	Comisión Asesora de Investigación Científica y Técnica, CAICYT (España)
Format:	artículo biblioteca
Language:	English
Published:	1984
Online Access:	http://hdl.handle.net/10261/21941 http://dx.doi.org/10.13039/501100007272
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