4.6 Article

Enantioselective Synthesis of Lepadins A-D from a Phenylglycinol-Derived Hydroquinolone Lactam

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 36, Pages 12804-12808

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501909

Keywords

alkaloids; asymmetric synthesis; lactams; nitrogen heterocycles; total synthesis

Funding

  1. Spanish Ministry of Economy and Competitiveness [CTQ2012-35250]
  2. AGAUR, Generalitat de Catalunya [2014SGR155]
  3. MINECO

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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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