The structure and absolute configuration of verticillol, a macrocyclic diterpene alcohol from the wood of sciadopitys verticillata sieb. et zucc. (taxodiaceae)

A verticillane‐type diterpene fromBoswellia carteriiessential oil

“…14 The absolute configuration of verticillol has been elaborated. 15 The verticillane and cembrane diterpene skeletons can be considered as biogenetically related and it was suggested that both cembranes and verticillanes have a common biogenetic precursor. 15 Although not proven, it is most likely that 8 and 9 have the same absolute configuration (Scheme 1).…”

Oxygenated verticillene derivatives from Bursera suntui

“…Previously, several epoxyverticillanes were obtained by oxidation of verticillenes with peroxyacids, such as m-chloroperoxybenzoic acid (Nagashima et al, 2005) and monoperphthalic acid (Karlsson et al, 1978), or by treatment with H 2 O 2 and SeO 2 in t-BuOH (Cerda- García-Rojas et al, 2007). Finally, allylic alcohols 9-11 are relevant because they closely resemble some structural features of the cytotoxic verticillenes cespitularins C and E isolated from the soft coral Cespitularia hypotentaculata (Duh et al, 2002).…”

“…These metabolites have been isolated from diverse sources such as the conifer Sciadopitys verticillata (Karlsson et al, 1978), the yew trees Taxus canadensis (Zamir et al, 1995(Zamir et al, , 1998, T. cuspidata (Renzulli et al, 2004), T. chinensis (Fang et al, 1995), T. chinensis var. mairei (Shi et al, 1998), and T. mairei (Shi et al, 2005), as well as the soft corals Cespitularia hypotentaculata (Duh et al, 2002) and C. taeniata (Shen et al, 2005), antipodal structures have also been found in the liverworts Jackiella javanica and Jungermannia infusca (Nagashima et al, 1997(Nagashima et al, , 2005.…”

Verticillane Derivatives from Natural Sources

“…It has been demonstrated that the cyclization mechanism from (E,E,E)-geranylgeranyl diphosphate to taxa-4,11-diene proceeds through a verticillen-12-yl carbocation intermediate [5]. Some hydroxylated verticillane derivatives have been isolated from diverse sources such as the conifer Sciadopitys verticillata [6], the dicotyledons Bursera suntui and B. kerberi [7], the soft coral Cespitularia hypotentaculata [8 -11], and the liverworts Jackiella javanica and Jungermannia infusca [12] [13]. Several polyfunctionalized derivatives of this bicyclic diterpene have also been isolated from Taxus species [14 -16].…”

“…Verticillane Diterpenoids from Liverworts and Other Plants. Verticillol (3), a crystalline alcohol, is the first verticillane diterpene which was isolated from the wood of conifer Sciadopitys verticillata in 1962 [1] [2], the configuration of this new type of diterpenes has been proposed as 4 on the basis of CD analysis of a norketodiepoxide derivative [6]. Howerer, this compound was re-studied by anomalous dispersion X-ray analysis of its 4-iodobenzoate derivative [5] and vibrational circular dichroism (VCD) spectral analysis [42].…”