A general approach to the basiliolide/transtaganolide natural products: total syntheses of basiliolide B, epi-8-basiliolide B, transtaganolide C, and transtaganolide D.
نویسندگان
چکیده
منابع مشابه
The total syntheses of basiliolide C, epi-basiliolide C, and protecting-group-free total syntheses of transtaganolides C and D.
The total syntheses of basiliolide C and previously unreported epi-basiliolide C are achieved by an Ireland-Claisen/Diels-Alder cascade. The development of a palladium catalyzed cross-coupling of methoxy alkynyl zinc reagents allows for the protecting-group-free syntheses of transtaganolides C and D. Syntheses of transtaganolides C and D are accomplished in a single operation to generate three ...
متن کاملTotal syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications.
Plants belonging to the genus Thapsia have been acknowledged since antiquity for their remarkable medicinal properties. Until very recently, this has been attributed to their primary chemical component thapsigargin (Figure 1a), a widely utilized and structurally complex sesquiterpenoid metabolite known for its potent SERCA inhibition. Within the past decade, an additional group of structurally ...
متن کاملBase-catalyzed Diels-Alder reactions of 2H-pyran-2,5-diones: a mild approach to basiliolide B.
A new class of base-catalyzed Diels-Alder reactions of 2H-pyran-2,5-diones has been developed using catalytic amount of dicyclohexylmethylamine in tert-butyl alcohol. This method has been successfully employed for construction of the tricyclic core of basiliolide B at room temperature with good yields and exclusive endo selectivity.
متن کاملA biomimetic synthesis of (±)-basiliolide B.
A highly diastereoselective and practical biomimetic total synthesis of (±)-basiliolide B has been achieved through the study of the two proposed biosynthetic pathways (O-methylation and O-acylation) for the unprecedented 7-methoxy-4,5-dihydro-3H-oxepin-2-one (C ring). The synthesis featured a cyclopropanation/ring opening strategy for establishing the stereogenic centers at C8 and C9, a biomim...
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A simple, highly diastereoselective, Lewis acid catalyzed Friedel-Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed. The method was applied for the enantiospecific total syntheses of structurally diverse natural products such as machaeriol-D, Δ(8)-THC, Δ(9)-THC, epi-perrottetinene and their analogues. Synthesis of both natural products and their enantiom...
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ورودعنوان ژورنال:
- Angewandte Chemie
دوره 50 16 شماره
صفحات -
تاریخ انتشار 2011