Two new derivatives of a recently-reported class of irregular diterpene have
been discovered in New Zealand species of the Apiaceae family.
16-Acetoxyanisotomenoic acid (8)
(3,3a,4,4-tetramethyl-3-{(Z)-5-acetoxy-4-methyl-3-pentenyl}-2,3,3a,4,5,6-hexahydro-1H-2-indenecarboxylic
acid) and anisotomene-1,12-diol (11)
(3,3a,4,4-tetramethyl-3-(2-hydroxy-4-methyl-3-pentenyl)-2,3,3a,4,5,6-hexahydro-1H-2-indenyl)
methanol) have been obtained from the sub-alpine plants,
Anisotome flexuosa and A. haastii
respectively. 13 C nuclear magnetic esonance (n.m.r.)
spectra of the anisotomene derivatives are complicated by line broadening.
Molecular modelling of anisotomenoic acid (1) and anisotomenol (2) suggests
that this is due to conformational exchange in the highly substituted bicyclo
[4,3,0] non-1-ene ring system.