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Closed Access item Dammarane triterpenes of Trevoa Trinervis: Structure and absolute stereochemstry of trevoagennins A, B, and C1

Authors:Betancor, Carmen
Freire, Raimundo
Hernández, Rosendo
Suárez, Ernesto
Cortés, Manuel
Prangé, Thierry
Pascard, Claudine
Issue Date:1983
Publisher:Royal Society of Chemistry (Great Britain)
Citation:Journal of the Chemical Society - Perkin Transactions 1 : 1119-1126 (1983)
Abstract:Trevoagenins A, B, and C, extracted from Trevoa trinervis Miers, are shown, by chemical and spectral means, to be isomeric dammarane triterpenes possessing the general 3,25,30-trihydroxy-(20,24)-epoxydammaran-16-one structure with stereoisomeric side-chains of the ocotillol type. Trevoagenin A (20R,24R)-(1), whose stereochemistry has been established by chemical methods and confirmed by X-ray analysis, was transformed into (20)R,24–ocotillone (26) and the C-24 stereochemistry was assigned as R. As a consequence, the C-24 stereochemistry for ocotillol-related compounds of the (20R)-series, unestablished so far, has been determined. The stereochemistry of trevoagenin B, (20S,24R)-(13), was established by chemical correlation with trevoagenin A. Moreover, trevoagenin B was transformed into ocotillol (20S,24R)-(21) and its recently questioned C-24 stereochemistry has been reaffirmed. Trevoagenin C, (20S,24S)-(17), is the C-24 isomer of trevoagenin B as shown by degradation of both compounds to the lactone (16).
Description:8 pages, 1 figure, 4 tables, 2 schemes.
Publisher version (URL):http://dx.doi.org/10.1039/P19830001119
URI:http://hdl.handle.net/10261/18131
ISMN:0300-922X
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