Enantioselective Synthesis of Lepadins A–D from a Phenylglycinol‐Derived Hydroquinolone Lactam. Issue 36 (21st July 2015)

• Record Type: Journal Article
• Authors: Amat, Mercedes; Pinto, Alexandre; Griera, Rosa; Bosch, Joan
• Is Part Of: Chemistry. Volume 21:Issue 36(2015)
• Page Start: 12804
• Page End: 12808
• Publication Date: 2015-07-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201501909
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The marine alkaloids (−)‐lepadins A–C and (+)‐lepadin D, belonging to two diastereoisomeric series, were synthesized from an (<italic>R</italic>)‐phenylglycinol‐derived tricyclic lactam via a common <italic>cis</italic>‐decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly of the <italic>cis</italic>‐decahydroquinoline platform, in the introduction of the C2 methyl and C3 hydroxy substituents, and in the generation of the C5 stereocenter.</p> </abstract>