Recent synthetic studies on the ergot alkaloids and related compounds

Somei, Masanori; Yokoyama, Yuusaku; Murakami, Yasuoki; Ninomiya, Ichiya; Kiguchi, Toshiko; Naito, Takeaki

doi:10.1016/s0099-9598(00)54003-6

Cited by 39 publications

(31 citation statements)

References 67 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 Among this family of natural products, lysergic acid 2 is the most widely recognized member and several semisynthetic derivatives are clinically used in the treatment of a range of neurological diseases. The dopamine agonists, pergolide 3 and bromocriptine, 4 are used for the treatment of Parkinson’s disease and type 2 diabetes, respectively, and ergometrine 5 is used as a uterotonic agent in combination with oxytocin.…”

Section: Introductionmentioning

confidence: 99%

“…1a,6 Herein, we report the total synthesis of dihydrolysergic acid ( 1 ) 7,8 and dihydrolysergol ( 2 ) 9 based on two key reactions we recently introduced. Notably, the latter natural product has only been prepared by semisynthesis from lysergic acid and the work herein discloses the first total synthesis of this natural product by an alternate route.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs

et al. 2015

View full text Add to dashboard Cite

The total syntheses of dihydrolysergic acid and dihydrolysergol are detailed based on a Pd(0)-catalyzed intramolecular Larock indole cyclization for the preparation of the embedded tricyclic indole (ABC ring system) and a subsequent powerful inverse electron demand Diels–Alder reaction of 5-carbomethoxy-1,2,3-triazine with a ketone-derived enamine for the introduction of a functionalized pyridine, serving as the precursor for a remarkably diastereoselective reduction to the N-methylpiperidine D-ring. By design, the use of the same ketone-derived enamine and a set of related complementary heterocyclic azadiene [4 + 2] cycloaddition reactions permitted the late stage divergent preparation of a series of alternative heterocyclic derivatives not readily accessible by more conventional approaches.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs

et al. 2015

View full text Add to dashboard Cite

show abstract

“…The intramolecular free radical cyclization of free acyl radicals generated from phenyl selenoesters proceeds ef®ciently and, in most cases, with little or no competing reduction or decarbonylation (Studer & Bossart, 2001). Compound (I) is thus a potential entry to ergot alkaloids (Somei et al, 2000), via an Uhle's ketone (Uhle, 1949;Teranishi et al, 1995) or a Kornfeld's ketone (Kornfeld et al, 1954(Kornfeld et al, , 1956. We report here the crystal structure of (I).…”

Section: Commentmentioning

confidence: 99%

Se-Phenyl 3-(1H-indol-3-yl)selenoacrylate

Meza¹,

Quintero²,

Bernès³

2004

Acta Cryst E

View full text Add to dashboard Cite

show abstract

“…15.5). (Fresneda and Molina, 2004;Kam and Choo, 2006;Kawasaki and Higuchi, 2005;Kn € olker, 2008;Mukherjee and Menge, 2000;Schardl et al, 2006;Somei and Yamada, 2004;Somei et al, 2000) This is the largest and most interesting alkaloid group derived from tryptophan. The important alkaloids from this group include simple tryptamine derivatives, carbazoles (where the ethanamine chain has been lost), a diversity of alkaloids where one or more prenyl residues are combined with tryptamine, and others where integration of regular monoterpenoid or diterpenoid units occurred.…”

Section: Classification Established Upon the Ring Structurementioning

confidence: 99%