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)

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