- Glutarimide Alkaloids Through Multicomponent Reaction Chemistry
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A concise four step synthetic route for glutarimide alkaloids of high biological interest is presented. The scaffold is accessed via an Ugi four component reaction, hereby introducing two points of variation. This is followed by a hydrolysis, a cyclization under mild conditions, and an amine deprotection. The diastereomers of the cyclized intermediate can be easily separated, thus leading to optically pure alkaloids. By this route, four natural products and ten derivatives were synthesized. The scope and limitations of the synthetic methodology were investigated.
- Konstantinidou, Markella,Kurpiewska, Katarzyna,Kalinowska-T?uscik, Justyna,D?mling, Alexander
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p. 6714 - 6719
(2018/11/25)
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- Synthesis of (-)-julocrotine and a diversity oriented Ugi-approach to analogues and probes
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An improved total synthesis of (-)-julocrotine in three steps from Cbz-glutamine, in 51% overall yield, is presented. To demonstrate the potential of the heterocyclic moiety for diversity oriented synthesis, a series of (-)-julocrotine analogues was synthesized by employing the heterocyclic precursor as an amino input in Ugi four-component reactions (Ugi-4CR) [1].
- Neves Filho, Ricardo A. W.,Westermann, Bernhard,Wessjohann, Ludger A.
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p. 1504 - 1507
(2012/01/06)
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- Enantioselective synthesis of glutarimide alkaloids cordiarimides A, B, crotonimides A, B, and julocrotine
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Five glutarimide alkaloids cordiarimide A (5), cordiarimide B (6), crotonimide A (3), crotonimide B (4), and julocrotine (2) have been synthesized starting from Boc-L-glutamine (7). The benzylic alcohol chiral centre of cordiarimides B (6) has been established in 6:1 diastereoselectivity by catalytic asymmetric hydrogenation using Zhou's catalytic system Pd(CF 3CO2)2/(R,R)-Me-DuPhos. Copyright
- Teng, Bo,Zheng, Jianfeng,Huang, Huiying,Huang, Peiqiang
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p. 1312 - 1318
(2011/10/31)
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- Synthesis of N -[(3 S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2 S)-2-methylbutanamide (( - )-julocrotine)
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The total synthesis of ( - )-julocrotine (1) starting from l-glutamic acid in 41% overall yield is described. The methodology utilizes protection, deprotection, and regioselection (carbonyl differentiation via oxazolidinone) protocols, and glutarimide ring formation is the key step.
- Silva, Luciano L.,Joussef, Antonio C.
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p. 1531 - 1534
(2011/08/21)
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