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Enantioselective synthesis of lepadins A D from a phenylglycinol-derived hydroquinolone lactam

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The marine alkaloids (-)-lepadins A-C and (+)-lepadin D, belonging to two diastereoisomeric series, were synthesized from an (R)-phenylglycinol-derived tricyclic lactam via a common cis-decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly of the cis-decahydroquinoline platform, in the introduction of the C2 methyl and C3 hydroxy substituents, and in the generation of the C5 stereocenter.

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AMAT TUSÓN, Mercedes, et al. Enantioselective synthesis of lepadins A D from a phenylglycinol-derived hydroquinolone lactam. Chemistry-A European Journal. 2015. Vol. 21, num. 36, pags. 12804-12808. ISSN 0947-6539. [consulted: 29 of June of 2026]. Available at: https://hdl.handle.net/2445/108026

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