124600-46-0Relevant academic research and scientific papers
An efficient synthesis of yuehchukene
Sheu, Jyh-Horng,Chen, Yua-Kuang,Hong, Yen-Long Vincent
, p. 1045 - 1046 (1991)
A three-step synthesis of yuehchukene 1, a novel dimeric indole natural product with anti-implantation activity via acid-catalyzed reaction of β-(3-hydroxy-3-methylbutenyl)indole is reported.
Reaction of (dimethylvinylidene)carbene with indole-3-carbaldehyde and its application in the synthesis of β-(dehydroprenyl)indole-based natural products
Sheu, Jyh-Horng,Chen, Chun-An,Chen, Buo-Horng
, p. 203 - 204 (1999)
Reaction of (dimethylvinylidene)carbene with indole-3-carbaldehyde gives various dehydroprenyl-based indoles. Efficient synthesis of the indole natural products yuehchukene and murrapanine, using this reaction as a key step, is also described.
Efficient Syntheses of Yuehchukene and β-(Dehydroprenyl)indole
Sheu, Jyh-Horng,Chen, Yua-Kuang,Hong, Yen-Long Vincent
, p. 5784 - 5787 (1993)
Yuehchukene (1) has been synthesized by one-step transformations of both alcohols (E)-β-(3-hydroxy-3-methylbutenyl)indole (3) and β-(1-hydroxy-3-methylbut-3-enyl)indole (4) under various reaction conditions.Alcohol 3 can be prepared efficiently from indole-3-carboxaldehyde (8) via a two-step reaction sequence.Alcohol 4, an isomer of 3, can be obtained from the same starting material 8 in only one step.Alcohol 4 can be converted directly into β-(dehydroprenyl)indole (2) in high yield under mild conditions via a base-induced dehydration.However, alcohol 3 does not give diene 2 under the same reaction conditions.Since diene 2 has been used as the key intermediate for the syntheses of yuehchukene (1), analogues of 1, and a cytotoxic compound, murrapanine (7), our present work also completes formal total syntheses of these bioactive compounds.
Short approach to bisindole alkaloid, yuehchukene, using 2-indolylcyanocuprate
Abe, Takumi,Komatsu, Hiroyuki,Ikeda, Toshiaki,Hatae, Noriyuki,Toyota, Eiko,Ishikura, Minoru
, p. 505 - 513 (2013/08/15)
A short total synthesis of a bisindole alkaloid, yuechukene, was achieved through the dimerization of β-dehydroprenylindole generated in situ from 1-(indol-3-yl)-3-methylbut-2-en-1-amine.
Fluorous synthesis of yuehchukene by α-lithiation of perfluoroalkyl-tagged 1-(arylsulfonyl)indole with mesityllithium
Naka, Hiroshi,Akagi, Yusuke,Yamada, Kyoko,Imahori, Tatsushi,Kasahara, Takahiro,Kondo, Yoshinori
, p. 4635 - 4637 (2008/03/12)
Lithiation chemistry has not been well explored in fluorous synthesis because of the lack of appropriate base-resistant fluorous tags; we recently developed a perfluoroalkylated arylsulfonyl tag for the protection of the indole ring nitrogen atom. Mesityl
A concise preparation of yuehchukene and its analogues
Ishikura, Minoru,Imaizumi, Katsuaki,Katagiri, Nobuya
, p. 2201 - 2220 (2007/10/03)
The palladium catalyzed carbonylative cross-coupling reaction of indolylborates (2) with vinyl triflates (3) afforded indol-2-yl ketones (4), which were subsequently converted to hexahydroindeno[2,1-b]indoles (5) with the aid of an acid. This protocol was well adapted for the total synthesis of yuehchukene.
Total synthesis of yuehchukene
Ishikura, Minoru,Imaizumi, Katsuaki,Katagiri, Nobuya
, p. 553 - 556 (2007/10/03)
Total synthesis of yuehchukene could be realized through the palladium catalyzed carbonylative cross-coupling reaction of indolylborate (2b) with cyclohexadienyl triflate (9) as a key reaction.
Broensted Acid Catalysed Electrophilic Substitution of Indole by Allylic Alcohols in Lithium Perchlorate-Diethyl Ether: Application to the Total Synthesis of Yuehchukene
Henry, Kenneth J.,Grieco, Paul A.
, p. 510 - 512 (2007/10/02)
A novel carbon-carbon bond-forming reaction between indole and β,β-disubstituted allylic alcohols in lithium perchlorate-diethyl ether containing a catalytic amount of a Broensted acid is described; the reaction has been applied to a total synthesis of yuehchukene.
Synthesis of yuehchukene and some analogues a general approach
Bergman, Jan,Venemalm, Lennart
, p. 759 - 768 (2007/10/02)
Yuehchukene and a number of structural analogues have been synthesized by intramolecular ring closure of α,β-unsaturated 2-acylindoles in the key step. Reduction of the resulting cyclopent[b]indol-3-one derivatives, followed by acid-catalyzed incorporatio
