Tricyclic sesquiterpenes from rudbeckia laciniata in honour of professor G. H. Neil Towers 75th birthday

Abstract Three phytotoxic sesquiterpenes were isolated from the roots of Rudbeckialaciniata , of which one of these was designated as lacinan-8-ol. Its absolute configuration was established by the MNCB [2-(2′-methoxy-1′-naphthyl)-3,5-dichlorobenzoic acid] method. It was chemically transformed into the corresponding secondary allylic alcohol, whose absolute configuration was also determined by MNCB and CD (circular dichroism) allylic benzoate methods.

[1]  B. Tomita,et al.  Allo-cedrol: A new tricarbocyclic sesquiterpene alcohol , 1973 .

[2]  A. Meyers,et al.  C2 symmetric amines. I. The asymmetric Ullmann synthesis of a new C2-symmetric binaphthyl , 1995 .

[3]  J. Mizutani,et al.  NOE CORRELATIONS IN MTPA, MNCB AND MBNC ESTERS , 1994 .

[4]  A. Lara,et al.  Novel tricyclic sesquiterpenes from Juniperus thurifera L. chemical confirmation of the duprezianane skeleton , 1996 .

[5]  A. Balaban.  Synthesis and spectra of pyrylo-trimethinecyanines , 1978 .

[6]  F. Bohlmann,et al.  Neue germacranolide aus Liatris cylindracea , 1979 .

[7]  G. Schmeda-Hirschmann,et al.  Sesquiterpenes from Fabiana imbricata , 1994 .

[8]  J. Lomas,et al.  Steric effects in the dehydration of tertiary alcohols by thionyl chloride-pyridine : an easy synthesis of tri--butyl-ethylene , 1971 .

[9]  R. M. King,et al.  A further steiractinolide derivative from Spilanthes leiocarpa , 1985 .

[10]  Jim-Min Fang,et al.  Terpenes from heartwood of Juniperus chinensis , 1996 .

[11]  R. M. King,et al.  The first 12.8β-germacrolide and other constituents from bolivian Stevia species , 1988 .

[12]  F. Bohlmann,et al.  Rudbeckiolid, ein dimeres Sesquiterpenlacton aus Rudbeckia laciniata , 1986 .

[13]  Trevor A. Mori,et al.  New cembrene diterpenes from the resins of Eremophila species , 1994 .

[14]  R. Curtis,et al.  centaurea rudbeckia spp. , 1965 .

[15]  F. Bohlmann,et al.  Neue norsesquiterpene aus Rudbeckia laciniata und Senecio paludaffinis , 1978 .

[16]  J. Mizutani,et al.  A new method for establishment of absolute configurations of secondary alcohols by NMR spectroscopy , 1994 .

[17]  A. Hassner,et al.  Direct room temperature esterification of carboxylic acids , 1978 .

[18]  D. Friedrich,et al.  Total synthesis of various elemanolides , 1988 .