Enantioselective Synthesis of Lepadins A–D from a Phenylglycinol‐Derived Hydroquinolone Lactam |
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| Authors: | Prof. Dr. Mercedes Amat Alexandre Pinto Dr. Rosa Griera Prof. Dr. Joan Bosch |
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| Affiliation: | Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona (Spain), Fax: (+34)?93‐402‐45‐39 http://www.ub.edu/sintefarma/ |
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| Abstract: | 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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| Keywords: | alkaloids asymmetric synthesis lactams nitrogen heterocycles total synthesis |
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