1106986-12-2Relevant academic research and scientific papers
Enantioselective Synthesis of Lepadins A-D from a Phenylglycinol-Derived Hydroquinolone Lactam
Amat, Mercedes,Pinto, Alexandre,Griera, Rosa,Bosch, Joan
, p. 12804 - 12808 (2015)
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. Using (R)-phenylglycinol as the source of chirality, the marine alkaloids (-)-lepadins A-C and (+)-lepadin D, with opposite absolute configuration at the C3 and C5 ring positions, have been synthesized. The synthesis features the use of a tricyclic oxazoloquinolone lactam as the key enantiomeric scaffold and proceeds via an advanced common decahydroquinoline intermediate.
