A biomimetic synthesis of (±)-basiliolide B.
نویسندگان
چکیده
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 biomimetic 2-pyrone Diels-Alder cycloaddition for the synthesis of the ABD ring system, and finally a highly efficient biomimetic intramolecular O-acylation for the C ring formation. This result provides an important perspective on the biosynthetic origin of the unprecedented 7-membered acyl ketene acetal moiety of the C ring.
منابع مشابه
A general approach to the basiliolide/transtaganolide natural products: total syntheses of basiliolide B, epi-8-basiliolide B, transtaganolide C, and transtaganolide D.
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ورودعنوان ژورنال:
- Angewandte Chemie
دوره 53 42 شماره
صفحات -
تاریخ انتشار 2014