Sciadopitys verticillata

Wood and leaves of Sciadopitys verticillata Sieb. et Zucc. 

An A-ray analysis of the diepoxide (135) derived from verticillol, which is obtained from the wood of Sciadopitys verticillata, has been used " to define the absolute configuration of this diterpenoid. The acid-catalysed cyclization of cembrene and isocembrenol, which leads to the formation of perhydrophenanth-rene derivatives, has been studied. 

The novelty of the carbon skeleton (2) named cleomane [10] present in cleomeolide was revealed by its NMR spectral data which demonstrated the occurrence of only one sp quaternary carbon atom, a structural feature unprecedented in naturally occurring diterpenes. A somewhat similar carbocyclic framework containing diterpene, verticillol (3) was isolated by Karlsson fit al- [13] from Sciadopitys verticillata more or less during the same period of time. 

The macrocylic diterpene alcohol, verticillol (3) was isolated from the wood of Sciadopitys verticillata Sieb. Et zucc. (Taxodiaceae) [13]. The structure of verticillol (3) was elucidated from NMR-LIS studies on it as well as its correlation to the diepoxide (14) whose structure was established by direct single crystal X-ray analysis. The absolute configuration of verticillol (3) was determined by CD data of the verticillol norketodiepoxide (15). The carbocyclic framework of verticillol (3) is somewhat akin to at of cleomeolide (1). However, the presence of the substituents(3-OH and C-8—>C-4 lactone) in appropriate positions in (1) facilitates its conversion to compounds analogous to taxane diterpenes. 

Nakane, S., Tanaka, T, Satouchi, K., Kobayashi, Y, Waku, K., Sugiura, T. (2000) Occurrence of a novel cannabimimetic molecule 2-sciadonoylglycerol (2-eicosa-5,ll,14-trienoylglycerol) in the umbrella pine Sciadopitys verticillata seeds. Biol. Pharm. Bull. 23, 758-761. 

Verticillanes such as (+)-verticillol from the wood of Sciadopitys verticillata (Taxodiaceae) rarely occur as natural products. 8,19-Cycloverticillane, however, is... 

Heartwoods of certain Taxus spp., especially that of T. baccata, contain several toxic diterpenoids, such as baccatin-IV (480) (264). About 30 compounds are known at present, and are invariably highly functionalized. The tricyclic framework of these compounds is readily rationalized by further cyclization of cembrene cation 473 (292). Verticillol (481), an extractive from the wood of Sciadopitys verticillata, corresponds to the bicyclic stage on the pathway to the taxane type (227). 

Sumimoto M 1963 Heartwood constituents of Sciadopitys verticillata Sieb. et Zucc. I. The con-stitustion of sciadin. Tetrahedron 19 643-655... 

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