68156-97-8Relevant academic research and scientific papers
Biomimetic Total Syntheses of Clavine Alkaloids
Chaudhuri, Saikat,Bhunia, Subhajit,Roy, Avishek,Das, Mrinal K.,Bisai, Alakesh
, p. 288 - 291 (2018/01/17)
Biomimetic total syntheses of either enantiomers of a number of ergot alkaloids, chanoclavine I (1b), chanoclavine I aldehyde (1c), pyroclavine (1e), festuclavine (1f), pibocin A (1g), 9-deacetoxyfumigaclavine C (1h), and fumigaclavine G (1i), have been achieved from seco-agroclavine (1a). The advanced intermediate for seco-agroclavine (1a) was synthesized via a key thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester.
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.
ERGOT ALKALOIDS: THE FIRST AND FIVE STEP TOTAL SYNTHESES OF (-)- AND (+)-6,7-SECOAGROCLAVINES, AND THE SYNTHESES OF (-)- AND (+)-6-NOR-6-PROPYL-6,7-SECOAGROCLAVINES ((-)- AND (+)-KSU 1415)
Nakagawa, Kyoko,Somei, Masanori
, p. 873 - 878 (2007/10/02)
Simple synthetic method for optically active 4,5-trans-((-)-and (+)- 6) and 4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindoles ((-)- and (+)-7) was developed.Using these chiral common synthetic intermediates, the first total syntheses of (-)- and (+)-6,7-secoagroclavines were achieved in only five steps.Preparations of (-)- and (+)-6-nor-6-propyl-6,7-secoagroclavines ((-)-and (+)-KSU 1415) are also described.
TOTAL SYNTHESES OF (+/-)-AGROCLAVINE-I, (+/-)-6-NOR-CHANOCLAVINE-II, AND (+/-)-CHANOCLAVINE-II
Somei, Masanori,Yamada, Fumio,Makita, Yoshihiko
, p. 895 - 898 (2007/10/02)
The first total syntheses of (+/-)-6-nor-chanoclavine-II and (+/-)-chanoclavine-II are achieved.Total synthesis of (+/-)-agroclavine-I is also reported.
TOTAL SYNTHESES OF CLAVINE ALKALOIDS BY AN INTRAMOLECULAR NITRONE-OLEFIN CYCLOADDITION REACTION
Oppolzer, W.,Grayson, J. I.,Wegmann, H.,Urrea, M.
, p. 3695 - 3706 (2007/10/02)
The racemic ergot alkaloids chanoclavine I (1) and 6,7-secoagroclavine (4) have been synthesized stereoselectively from indole-4-carboxaldehyde (7) in overall yields of 14 and 13 percent, respectively.Further syntheses of isochanoclavine I (2), paliclavine (5) and costaclavine (6), via the same isoxazolidine 18 are described.The key step 16-->18 (Scheme 4) involves a transient nitrone 17 which undergoes a kinetically controlled, regio- and stereoselective intramolecular cycloaddition to a 1,2-disubstituted olefinic bond.
TOTAL SYNTHESIS OF ERGOT ALKALOID, (+/-)-6,7-SECOAGROCLAVINE
Somei, Masanori,Yamada, Fumio,Karasawa, Yoshio,Kaneko, Chikara
, p. 615 - 618 (2007/10/02)
Ergot alkaloid, (+/-)-6,7-secoagroclavine was synthesized form 2-methyl-5-nitroisoquinolinium iodide by three routes.In the course of the study, a novel intra-molecular γ-alkylation of allyl alcohol was found.Reaction of Grignard reagents with nitroalkanes to afford N-alkyl hydroxylamines was effectively used in the present synthesis.
TOTAL SYNTHESIS OF (+/-)-6,7-SECOAGROCLAVINE
Natsume, Mitsutaka,Muratake, Hideaki
, p. 1101 - 1105 (2007/10/02)
An ergot alkaloid 6,7-secoagroclavine was synthesized in racemic form from 1-methoxycarbonylpyrrole in 15 steps.
