有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
(−)-FR182877の不斉全合成
鈴木(田中) 奈津美鈴木 孝洋松村 岳彦細谷 洋介中里 知幸中田 雅久
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2011 年 69 巻 6 号 p. 646-660

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An enantioselective total synthesis of (−)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (−)-FR182877 with the correct new seven stereogenic centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membered F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the α-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (−)-FR182877.

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