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Non-Citizen Residents and Representative Democracy : Beyond Electoral Representation
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Strafrecht Allgemeiner Teil Memorandum (6) : Revision der „Irrtum - und Vorsatzlehre“
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Framework of the Compensation Fund Based on Product Liability of the Manufacturers of Building Materials that Contain Toxic Asbestos for the Victims of Occupational Accidents
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Commodified and Criminalized : New Racism and Structural Violence in Nana Kwame Adjei-Brenyah’s Friday Black
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The King of Alsander by James Elroy Flecker : Romanticism in an Unromantic Age
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Doctor - Patient Relationship in Psychiatric Medicine, Part 3 : An Introduction to the Contract Law of Psychiatric Medicine
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Strafrecht Allgemeiner Teil Memorandum (5) III : Rechtstheorie der ,,vorsätzlichen Nebentäterschaft‘‘
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The Landfill of Henoko in Okinawa and the Instruction of the Government
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Total Syntheses of Biosynthetic Intermediates Toward Collective Supply of Biologically Active Alkaloid and Total Synthesis of (—)-Rubenine
Get PDFThe 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.departmental bulletin pape