Clerodane diterpenoids and an ursane triterpenoid from Salvia haenkei. Computer-assisted structural elucidation

Almanza, G., Balderrama, L., Labbé, C., Lavaud, C., Massiot, G., Nuzillard, J.-M., Connolly, J. D., Farrugia, L. J. and Rycroft, D. S. (1997) Clerodane diterpenoids and an ursane triterpenoid from Salvia haenkei. Computer-assisted structural elucidation. Tetrahedron, 53(43), pp. 14719-14728. (doi:10.1016/S0040-4020(97)00943-5)

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Abstract

Five ent-clerodane diterpenoids, four new, and a new ursane triterpenoid have been isolated from Salvia haenkei collected in Bolivia. The structures of two ent-clerodanes, ent-(4S,5R)-7α-acetoxy-15,16-epoxy-10-oxo-9,10-secocleroda-1,8,13(16),14-tetraene-17,12S;18,19-diolide 1 (salvianduline B) and ent-(5R,9R)-15,16-epoxy-10S-hydroxy-cleroda-3,7,13(16),14-tetraene-17,12S;18,19-diolide 2, were elucidated from HMQC and HMBC data using an automatic structure elucidation computer program. The structures of the other clerodanes, ent-(5R,9R)-15,16-epoxy-10S-hydroxy-cleroda-3,13(16),14-triene-17,12S;18,19-diolide 6, ent-(4S,5R,9S,10R)-15,16-epoxycleroda-1,13(16),14-triene-17,12S;18,19-diolide 7 and ent-(5R,9R,10S)-7S-acetoxy-15,16-epoxy-1S,2S,12ξ-trihydroxycleroda-3,13(16),14-trien-18,19-olide 8, were derived in the usual manner from 1H and 13C NMR data. The stereochemistry of 2 was confirmed by an X-ray crystal structure analysis. The triterpenoid is 3-oxours-12-ene-1β,11α-diol 9.

Item Type:Articles
Keywords:Natural product chemistry.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Connolly, Professor Joseph and Farrugia, Dr Louis and Rycroft, Dr David
Authors: Almanza, G., Balderrama, L., Labbé, C., Lavaud, C., Massiot, G., Nuzillard, J.-M., Connolly, J. D., Farrugia, L. J., and Rycroft, D. S.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
Publisher:Elsevier Science
ISSN:0040-4020
ISSN (Online):1464-5416

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