Photocyclization of Enamides. XXXIII. Total Syntheses of (±)-Agroclavines, (±)-Fumigaclavine B, and (±)-Lysergene

Photocyclization of Enamides. XXXIII. Total Syntheses of (±)-Agroclavines, (±)-Fumigaclavine B, and (±)-Lysergene

Total syntheses of several ergoline-type alkaloids, (±)-agroclavine (21), (±)-agroclavine I (24), (±)-fumigaclavine B (28), and (±)-lysergene (33), were accomplished via a route involving reductive photoxyclization of the enamide 5 followed by oxidative cleavage of the dihydrofuran ring.

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1991/01/25, Vol.39(1), pp.23-30
Hauptverfasser: NINOMIYA, Ichiya, KIGUCHI, Toshiko, HASHIMOTO, Chiyomi, NAITO, Takeaki
Format: Artikel
Sprache:eng
Schlagworte:
agroclavine
agroclavine I
enamide
ergot alkaloid
fumigaclavine B
lysergene
reductive photocyclization
total syntheses
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Zusammenfassung:Total syntheses of several ergoline-type alkaloids, (±)-agroclavine (21), (±)-agroclavine I (24), (±)-fumigaclavine B (28), and (±)-lysergene (33), were accomplished via a route involving reductive photoxyclization of the enamide 5 followed by oxidative cleavage of the dihydrofuran ring.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.39.23