Synonyms:6,8b-Ethano-8bH-cyclopenta(de)-2-benzopyran-1,4-dione, octahydro-10,10-dimethyl-, (3aalpha,5abeta,6alpha,8aalpha,8balpha)-;quadrone
99% *data from raw suppliers
There total 4 articles about Quadrone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
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The research focuses on the synthesis of bridged bicycloalkanes through the alicyclic Claisen rearrangement, with the aim of achieving a formal total synthesis of (+)-quadrone. The study explores the extension of a methodology initially used for hetero- and carbocycle synthesis to the preparation of bridged bicycloalkanes, with quadrone being a target molecule due to its unique tetracyclic topology and significant antineoplastic properties. The researchers successfully synthesized quadrone in a stereospecific, 13-step process from carbomethoxy enone 6, utilizing various chemicals including ketene acetal 4, eight-membered lactone 5, and ester 3 (R = SiMe2-t-Bu), among others. The synthesis involved the rearrangement of lactone 5 to silyl ester 3, followed by oxidation of the olefinic functionality in acid 3 to yield diketo acid 2, which was identical to a sample provided by Professor Schlessinger. The study concludes that the alicyclic Claisen rearrangement is a feasible approach for the preparation of bridged bicycloalkanes and holds promise for further development in organic synthesis.
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