Synthetic studies towards the ent-labdane diterpenoids: rearrangement of ent-halimanes.
نویسندگان
چکیده
For the first time ent-labdanes have been synthetised starting from ent-halimic acid, following a route that is the reverse of the biosynthetic one leading to the former compounds.
منابع مشابه
Functional characterization of wheat copalyl diphosphate synthases sheds light on the early evolution of labdane-related diterpenoid metabolism in the cereals.
Two of the most agriculturally important cereal crop plants are wheat (Triticum aestivum) and rice (Oryza sativa). Rice has been shown to produce a number of diterpenoid natural products as phytoalexins and/or allelochemicals--specifically, labdane-related diterpenoids, whose biosynthesis proceeds via formation of an eponymous labdadienyl/copalyl diphosphate (CPP) intermediate (e.g., the ent-CP...
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A route for the degradation of the side chain of ent-labdane derivatives has been devised, giving the useful synthon 2beta,12-dihydroxy-13,14,15,16,17-pentanor-ent-labdane-8-one (8). The use of this compound in the preparation of terpenylquinone derivatives shall be reported elsewhere. In addition we have synthesized the compound 2beta,12-diacetoxy-8beta,17-epoxy-13,14,15,16-tetranor-ent-labdan...
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Three new rearranged ent-kaurane-type diterpenoids (1-3) and seven new ent-kaurane-type diterpenoids (4-10) have been isolated from the liverwort Jungermannia atrobrunnea. Their structures were determined by extensive spectroscopic techniques and X-ray crystallographic analysis. The absolute configurations of these compounds were clarified by CD spectroscopic studies. Compound 1 is the first ex...
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A selective route for the degradation of the unsaturated side chain of ent-labdanes has been devised, giving two useful synthons: 2beta-acetoxy-14,15,17-trinor-ent-labdane-8,13- dione (5) and 2beta-acetoxy-14,15-dinor-ent-labd-8(17)-en-13-one (7), the use of which for the preparation of terpenylquinone derivatives shall be reported elsewhere.
متن کاملA Pair of Residues That Interactively Affect Diterpene Synthase Product Outcome
The labdane-related diterpenoids (LRDs) are an important superfamily of natural products whose structural diversity critically depends on the hydrocarbon skeletal structures generated, in large part, by class I diterpene synthases. In the plant kingdom, where the LRDs are predominantly found, the relevant class I diterpene synthases are clearly derived from the ent-kaurene synthase (KS) require...
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ورودعنوان ژورنال:
- Molecules
دوره 11 10 شماره
صفحات -
تاریخ انتشار 2006