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Please use this identifier to cite or link to this item: http://hdl.handle.net/10928/1497

Title: 生物活性アルカロイドの集団的供給を志向した生合成中間体の全合成および(-)-ルベニンの全合成
Other Titles: Total Syntheses of Biosynthetic Intermediates Toward Collective Supply of Biologically Active Alkaloid and Total Synthesis of (—)-Rubenine
Authors: 楽満, 憲太
Keywords: alkaloids
total synthesis
Issue Date: 1-Dec-2021
Publisher: 成蹊大学理工学部
Abstract: The first enantioselective total syntheses of the biosynthetic intermediates of the monoterpenoid indole alkaloids, (—)- secologanin (1), (—)-5-carboxystrictosidine (2), and (—)-strictosidine (3), were accomplished. In addition, (—)-rubenine (4) with a hexa-continuous fused ring was synthesized. The key reactions to form a dihydropyran ring of 1 was a sequential anti- and enantioselective organocatalytic Michael reaction/Fukuyama reduction. The secologanin tetraacetate (15), which is a key intermediate for our bioinspired collective syntheses of monoterpenoid indole alkaloids, was prepared in multigram scales. In the bioinspired Pictet-Spengler reaction for the synthesis of 2 and 3, it was important to use L-tryptophan methyl ester and cyanotryptamine derived from D-tryptophan, respectively, as substrate to achieve the desired diastereoselectivity. The total synthesis of 4 were achieved by epoxidation and nucleophilic cyclization of secondary amine followed by a lactonization reaction as in biosynthesis.
URI: http://hdl.handle.net/10928/1497
Appears in Collections:第58巻第2号

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