- Pd(II)-catalyzed annulation reactions of epoxides with benzamides to synthesize isoquinolones
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Epoxides as alkylating reagents are unprecedentedly applied in Pd(II)-catalyzed C?H alkylation and oxidative annulation of substituted benzamides to synthesize isoquinolones rather than isochromans, which is accomplished through alerting the previously reported reaction mechanism by the addition of oxidant and TEA. Under these conditions, various isoquinolones have been prepared with yields up to 92%. In addition, this methodology has been successfully employed in the total syntheses of rupreschstyril, siamine, and cassiarin A in an expedient fashion.
- Wang, Huihong,Cao, Fei,Gao, Weiwei,Wang, Xiaodong,Yang, Yuhang,Shi, Tao,Wang, Zhen
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p. 863 - 868
(2021/02/06)
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- First total synthesis of cassiarin A, a naturally occurring potent antiplasmodial alkaloid
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The first total synthesis of cassiarin A, an antiplasmodial alkaloid isolated from Cassia siamea, was achieved via sequential alkynylation of arenes with Sonogashira coupling and 6-endo-dig-cyclization of phenolic oxygens to the resulting alkynes.
- Rudyanto, Marcellino,Tomizawa, Yuichiro,Morita, Hiroshi,Honda, Toshio
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supporting information; experimental part
p. 1921 - 1922
(2009/04/10)
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- Vinyl Azides in Heterocyclic Synthesis. Part 9. Synthesis of the Isoquinolone Alkaloid Siamine by Intramolecular Aza-Wittig Reaction
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The isoquinolone alkaloid siamine (1) has been synthesised from 3,5-dibenzyloxybenzoic acid (2) by a route which incorporates an intramolecular aza-Wittig reaction as the key step.The benzaldehyde (5), prepared from the benzoic acid (2) by the dihydro-oxa
- Kennedy, Michael,Moody, Christopher J.,Rees, Charles W.,Vaquero, Juan J.
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p. 1395 - 1398
(2007/10/02)
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