Total Synthesis of the Marine Alkaloids (−)-Lepadins A, B, and C Based on Stereocontrolled Intramolecular Acylnitroso-Diels−Alder Reaction

The first syntheses of (−)-lepadins A and C, as well as a new synthesis of (−)-lepadin B, have been achieved from commercially available (S)-malic acid. The methodology is based on an intramolecular hetero-Diels−Alder reaction of the acylnitroso compound, affording the bicyclic oxazino lactam with t...

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Veröffentlicht in:	Journal of organic chemistry 2001-05, Vol.66 (10), p.3338-3347
Hauptverfasser:	Ozawa, Tetsuji, Aoyagi, Sakae, Kibayashi, Chihiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 2-Ring - chemistry Marine Biology Molecular Conformation Quinolines Solvents - pharmacology Stereoisomerism
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