- Reaction of (dimethylvinylidene)carbene with indole-3-carbaldehyde and its application in the synthesis of β-(dehydroprenyl)indole-based natural products
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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.
- Sheu, Jyh-Horng,Chen, Chun-An,Chen, Buo-Horng
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p. 203 - 204
(2007/10/03)
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- Further study on the transformation of β-(1-hydroxybut-3-enyl)-indoles into 1-β-(indolyl)buta-1,3-diene, yuehchukene, murrapanine and analogues
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β-(1-Hydroxybut-3-enyl)indoles have been converted into three indole natural products: yuehchukene 1, β-(dehydroprenyl)indole 2, murrapanine 3 and other analogues in a one step procedure under various acid-catalysed reaction conditions in THF. A one-pot synthesis of bisnoryuehchukene 15 starting from indole-3-carboxaldehyde was also achieved using a similar approach. β-(1-Hydroxybut-3-enyl)indoles are presumed to be dehydrated to 1-(β-indolyl)buta-1,3-dienes which then react further to give yuehchukene, murrapanine and other derivatives via a Diels-Alder pathway. The yields of 3 and normurrapanine 31 could be improved by using an aerial oxidation method. Murrapanine and analogues were found to exhibit potent cytotoxicity towards various cancer cell lines.
- Sheu, Jyh-Horng,Chen, Yua-Kuang,Chung, Huey-Fen,Lin, Song-Fang,Sung, Ping-Jyun
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p. 1959 - 1965
(2007/10/03)
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- Synthesis of yuehchukene analogues, murrapanine and normurrapanine utilizing thermal reaction of β-(1-hydroxybutenyl)indoles under neutral reaction conditions
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β-(1-Hydroxybutenyl)indoles, which were prepared in high yields from indole-3-carboxaldehyde, could be converted into yuehchukene analogues (8a, b), murrapanine(9a)and normurrapanine(9b)m one step under thermal-induced reaction conditions in neutral solution of ethylene glycol and water. β-(1-Hydroxybutenyl)indoles are supposed to be dehydrated to 1-(β-indolyl)-1,3-butadienes which react further to yuehchukene analogues via a Diels-Alder pathway. Murrapanine and normurrapanine showed a cytotoxicity toward KB cells.
- Sheu, Jyh-Horng,Chen, Yua-Kuang,Chung, Huey-Fen,Sung, Ping-Jyun,Lin, Song-Fong
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p. 1751 - 1758
(2007/10/03)
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- STRUCTURE AND SYNTHESIS OF MURRAPANINE, A NOVEL SKELETAL INDOLE-NAPHTHOQUINONE ALKALOID AND CYTOTOXIC PRINCIPAL FROM MURRAYA PANICULATA VAR. OMPHALOCARPA
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A novel skeletal cytotoxic indole-naphthoquinone alkaloid, murrapanine, has been isolated from the root bark of Murraya paniculata var. omphalocarpa and its structure has been established from spectral data and single-crystal X-ray analysis; the synthesis of murrapanine from indole-3-aldehyde is also described.
- Wu, Tian-Shung,Liou, Meei-Jen,Lee, Chwan-Jen,Jong, Ting-Ting,McPhail, Andrew T.,et al.
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p. 6649 - 6652
(2007/10/02)
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