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

Ichiya NINOMIYA; Toshiko KIGUCHI; Chiyomi HASHIMOTO; Takeaki NAITO

doi:10.1248/cpb.39.23

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

Ichiya NINOMIYA, Toshiko KIGUCHI, Chiyomi HASHIMOTO, Takeaki NAITO

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Keywords: enamide, reductive photocyclization, ergot alkaloid, agroclavine, agroclavine I, fumigaclavine B, lysergene, total syntheses

JOURNAL FREE ACCESS

1991 Volume 39 Issue 1 Pages 23-30

DOI https://doi.org/10.1248/cpb.39.23

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Abstract

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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