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- W3099856853 abstract "Josep Bonjoch of the Universitat de Barcelona extended (Org. Lett. 2013, 15, 326) the Jørgensen variation of the Robinson annulation to the amine-substituted β-keto ester 1. The product cis-fused sulfonamide 3, readily brought to high ee by recrystallization, was carried onto (+)-lycoposerramine Z 4. Intramolecular ketene 2+2 cycloaddition is underdeveloped as a synthetic method. Kozo Shishido of the University of Tokushima observed (Org. Lett. 2013, 15, 200) high diastereoselectivity in the cyclization of 5 to 6. This set the stage for the synthesis of (-)-esermethole 7. Jieping Zhu of the Ecole Polytechnique Fédérale de Lausanne prepared (Angew. Chem. Int. Ed. 2013, 52, 3272) the cyclopentene 8 by coupling the alkenyl triflate with the salt of an α-alkyl arylacetic acid. Ozonolysis followed by reductive work-up led to a diamino keto aldehyde that cyclized to 9. Benzyl ether cleavage delivered (±)-goniomitine 10. Richard J.K. Taylor of the University of York developed (Angew. Chem. Int. Ed. 2013, 52, 1490) a powerful tandem conjugate addition-imination-methanolysis protocol. He had already prepared (+)-grandisine 11 from N-Boc prolinol. Amination-imination converted 11 to (+)-grandisine 12. This was opened by methanolysis to (+)-grandisine G 13. Four diastereomers are possible from the condensation of 14 and 15. Eric N. Jacobsen of Harvard University developed (Org. Lett. 2013, 15, 706) an organocatalyst that delivered 16 as the dominant diastereomer. This was readily converted to (+)-reserpine, the enantiomer of the natural product." @default.
- W3099856853 created "2020-11-23" @default.
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- W3099856853 date "2015-01-08" @default.
- W3099856853 modified "2023-09-26" @default.
- W3099856853 title "Alkaloid Synthesis: Lycoposerramine Z (Bonjoch), Esermethole (Shishido), Goniomitine (Zhu), Grandisine (Taylor), Reserpine (Jacobsen)" @default.
- W3099856853 doi "https://doi.org/10.1093/oso/9780190200794.003.0061" @default.
- W3099856853 hasPublicationYear "2015" @default.
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