194346-16-2Relevant articles and documents
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Taylor,Ramstad
, p. 681,682, 683 (1961)
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Controlling a structural branch point in ergot alkaloid biosynthesis
Cheng, Johnathan Z.,Coyle, Christine M.,Panaccione, Daniel G.,O'Connor, Sarah E.
, p. 12835 - 12837 (2010)
The ergot alkaloids are a diverse class of fungal-derived indole alkaloid natural products with potent pharmacological activities. The biosynthetic intermediate chanoclavine-I aldehyde 1 represents a branch point in ergot biosynthesis. Ergot alkaloids festuclavine 2 and agroclavine 3 derive from alternate enzymatic pathways originating from the common biosynthetic precursor chanoclavine-I aldehyde 1. Here we show that while the Old Yellow Enzyme homologue EasA from the ergot biosynthetic gene cluster of Aspergillus fumigatus acts on chanoclavine-I aldehyde 1 to yield festuclavine 2, EasA from Neotyphodium lolii, in contrast, produces agroclavine 3. Mutational analysis suggests a mechanistic rationale for the switch in activity that controls this critical branch point of ergot alkaloid biosynthesis.
Synthesis and incorporation of a 14C-and 3H-labeled 4-dimethylallyl-tryptophan and a 14C-labeled 4-dimethylallyl-tryptamine as well as incorporation of a 14C-labelled Dimethylallyl-pyrophosphate
Plieninger,Immel,V?lkl
, p. 223 - 229 (1967)
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Regioselective Direct C-4 Functionalization of Indole: Total Syntheses of (-)-Agroclavine and (-)-Elymoclavine
Lv, Jianbo,Wang, Bin,Yuan, Kuo,Wang, Yuan,Jia, Yanxing
, p. 3664 - 3667 (2017)
An efficient rhodium-catalyzed method for direct C-H functionalization at the C4 position of unprotected indoles has been developed. The utility of this method is demonstrated by the concise total syntheses of agroclavine and elymoclavine in a divergent manner. These syntheses feature a Pd-catalyzed asymmetric allylic alkylation reaction to assemble the triyclic indole moiety, and a ring-closing metathesis reaction to form the D ring.
Synthetic studies directed toward ergot alkaloids, (±)-6,7-secoagroclavine, (±)-chanoclavine-1, (±)-chanoclavine-II, and (±)-agroclavine-I, by an efficient and common synthetic route
Yamada, Fumio,Makita, Yoshihiko,Somei, Masanori
, p. 599 - 620 (2008/03/12)
Novel three synthetic routes to (±)-6,7-secoagroclavine were developed from either methyl 3-(3-formylindol-4-yl)acrylate, indole-4-carbaldehyde, or 4-iodoindole-3-carbaldehyde. The total syntheses of (±)-chanoclavine-I, (±)-chanoclavine-II, and (±)-agroclavine-I were accomplished as well from the synthetic intermediates involved in the synthesis of (±)-6,7-secoagroclavine, culminating in establishing an efficient and common synthetic method for ergot alkaloids.