Synthesis of Marine Diterpene Isocyanide (−)-Kalihinol Y and Diterpene Isothiocyanate (−)-10-Epi-kalihinol I
نویسندگان
چکیده
منابع مشابه
Total synthesis of antimalarial diterpenoid (+)-kalihinol A.
Total synthesis of antimalarial diterpenoid (+)-kalihinol A, isolated from marine sponge Acanthella sp., is achieved. This total synthesis involves regioselective alkylation of an epoxide, construction of a tetrahydropyran ring by iodo-etherification, construction of a cis-decalin ring by intramolecular Diels-Alder reaction, isomerization of cis-decalin to trans-decalin, and subsequent function...
متن کاملSynthesis and Potent Antimalarial Activity of Kalihinol B
Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of k...
متن کاملAntimalarial Properties of Simplified Kalihinol Analogues
Several kalihinol natural products, members of the broader isocyanoterpene family of antimalarial agents, are potent inhibitors of Plasmodium falciparum, the agent of the most severe form of human malaria. Our previous total synthesis of kalihinol B provided a blueprint to generate many analogues within this family, some as complex as the natural product and some much simplified and easier to a...
متن کاملSynthesis of ent-kaurane diterpene monoglycosides.
Synthesis of two ent-kaurane diterpene glycosides, steviol 19-O-β-D-glucopyranosiduronic acid (steviol glucuronide, 5), and 13-hydroxy ent-kaur-16-en-19-oic acid-β-D-glucopyranosyl ester (7) has been achieved from a common starting material, steviol, using phase transfer catalyst. Also, synthesis of an additional 17-nor-ent-kaurane glycoside, namely 13-methyl-16-oxo-17-nor-ent-kauran-19-oic aci...
متن کاملSynthesis and sensory evaluation of ent-kaurane diterpene glycosides.
Catalytic hydrogenation of the three ent-kaurane diterpene glycosides isolated from Stevia rebaudiana, namely rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH)₂ and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on ...
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ژورنال
عنوان ژورنال: Chemical and Pharmaceutical Bulletin
سال: 2012
ISSN: 0009-2363,1347-5223
DOI: 10.1248/cpb.c12-00485