33062-26-9Relevant articles and documents
SYNTHESES OF (+/-)-CLAVICIPITIC ACID AND ITS DERIVATIVES
Somei, Masanori,Hamamoto, Shoichi,Nakagawa, Kyoko,Yamada, Fumio,Ohta, Toshiharu
, p. 719 - 724 (1994)
A formal total synthesis of (+/-)-clavicipitic acid was achieved in five steps from indole-3-carboxaldehyde.Syntheses of (+/-)-4-cyano-, (+/-)-4-methyl-, and (+/-)-4-hydroxymethyl-6-(2-methyl-1-propen-1-yl)-3,4,5,6-tetrahydro-1H-azepinoindoles are also reported.
Efficient total synthesis of (-)-cis-clavicipitic acid
Xu, Zhengren,Li, Qingjiang,Zhang, Lihe,Jia, Yanxing
, p. 6859 - 6862 (2009)
An efficient total synthesis of (-)-cis-clavicipitic acid has been achieved in seven linear steps (42% overall yield) from the known compound 6. The present synthesis features a palladium-catalyzed indole synthesis to provide the optically pure 4-chlorotr
Total Synthesis of the Clavicipitic Acids by an Intramolecular Azide Cycloaddition Strategy
Kozikowski, P.,Greco, Michael N.
, p. 2310 - 2314 (1984)
A straightforward total synthesis approach to the structurally unique ergot derailment products, the clavicipitic acids 1 and 2, is described.The synthetic strategy is based on the formation of the seven-membered nitrogen-containing ring of 1 and 2 through an intramolecular azide cycloaddition process.The cycloaddition strategy, which produces solely the imine product 24, does in some sense mimic the proposed biosynthetic pathway to these acids.
Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis
Chein, Rong-Jie,Chen, Kuan-Lin,Lai, Chen-Yu,Lin, Hsiao-Ching,Pham, Mai-Truc,Tang, Yi
, (2020)
(-)-Aurantioclavine (1), which contains a characteristic seven-membered ring fused to an indole ring, belongs to the azepinoindole class of fungal clavine alkaloids. Here we show that starting from a 4-dimethylallyl-l-tryptophan precursor, a flavin adenine dinucleotide (FAD)-binding oxidase and a catalase-like heme-containing protein are involved in the biosynthesis of 1. The function of these two enzymes was characterized by heterologous expression, in vitro characterization, and deuterium labeling experiments.
Total Synthesis of (-)-Clavicipitic Acid via γ,γ-Dimethylallyltryptophan (DMAT) and Chemoselective C-H Hydroxylation
Bartoccini, Francesca,Venturi, Silvia,Retini, Michele,Mari, Michele,Piersanti, Giovanni
, p. 8027 - 8034 (2019/06/17)
The first total synthesis of natural (-)-clavicipitic acid from ?,?-dimethylallyltryptophan (DMAT), its biosynthetic precursor, is described. This is done by regio- and chemoselective, remote, nondirected C(sp3)-H hydroxylation followed by amin
Synthesis of (±)- cis -clavicipitic acid by a Rh(I)-catalyzed intramolecular imine reaction
Bartoccini, Francesca,Casoli, Mariangela,Mari, Michele,Piersanti, Giovanni
, p. 3255 - 3259 (2014/05/06)
A new and short synthesis of racemic cis-clavicipitic acid was achieved by taking advantage of the double nucleophilic character of indole-4-pinacolboronic ester. Key to the success of the synthesis were an efficient and selective C-3 indole Friedel-Craft
Total synthesis of clavicipitic acid and aurantioclavine: Stereochemistry of clavicipitic acid revisited
Xu, Zhengren,Hu, Weimin,Liu, Qiang,Zhang, Lihe,Jia, Yanxing
scheme or table, p. 7626 - 7635 (2011/02/25)
The stereocontrolled total synthesis of clavicipitic acid and aurantioclavine from a common azepino[5,4,3-cd]-indole intermediate is reported. This key azepinoindole nucleus was constructed via a one-pot Heck/Boc-deprotection/aminocyclization process from
Enantioselective synthesis of (-)-cis-clavicipitic acid
Ku, Jin-Mo,Jeong, Byeong-Seon,Jew, Sang-Sup,Park, Hyeung-Geun
, p. 8115 - 8118 (2008/02/12)
(Chemical Equation Presented) An enantioselective synthetic method for (-)-cis-clavicipitic acid (1) was reported. 1 was obtained in 10 steps (99% ee and 20% overall yield) from 1H-indole-3-carboxylic acid methyl ester (9) via asymmetric phase-transfer ca
Syntheses without protection: A three-step synthesis of optically active clavicipitic acid by utilizing biomimetic synthesis of 4-bromotryptophan
Yokoyama, Yuusaku,Hikawa, Hidemasa,Mitsuhashi, Masaharu,Uyama, Aki,Murakami, Yasuoki
, p. 7803 - 7806 (2007/10/03)
The optically active clavicipitic acid (4), an ergot alkaloid, was synthesized by a three-step sequence from 4-bromoindole (1). The reaction of 1 with dl-serine (2) in the presence of Ac2O followed by enzymatic kinetic resolution gave (S)-4-bromotryptophan (3). The Heck reaction of 3 with 1,1-dimethylallylalcohol in aqueous media gave clavicipitic acid in one-pot.
A SHORT STEP SYNTHESIS OF CLAVICIPITIC ACIDS FROM 4-CYANOMETHYLINDOLE
Matsumoto, Masakatsu,Kobayashi, Hisako,Watanabe, Nobuko
, p. 1197 - 1202 (2007/10/02)
4-(3-methyl-1-oxo-2-buten-1-yl)indole (3) was efficiently synthesized from 4-cyanomethyl-1-(p-toluenesulfonyl)indole by alkylation with 2-methyl-2-buten-1-yl tosylate and by successive aerobic oxidation and deprotection of N-tosyl group.The acylindole 3 was used for a short step synthesis of clavicipitic acids (4).
