- Metal-Free and Versatile Synthetic Routes to Natural and Synthetic Prodiginines from Boron Dipyrrin
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Prodiginines, as a family of bacterial alkaloids, possess a number of interesting biological activities. New, concise synthetic routes for the facile preparation of both synthetic and natural prodiginines in good yields have been developed, which use BODIPY functionalization reactions, such as condensation, nucleophilic substitution, and BF2 deprotection. This new metal-free synthetic method opens the door toward a wide variety of C-ring functionalized prodiginines, including those that are not possible to obtain through current synthetic methods, for their advanced biological activities.
- Li, Jin,Zhang, Qian,Yin, Jian,Yu, Changjiang,Cheng, Kai,Wei, Yun,Hao, Erhong,Jiao, Lijuan
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supporting information
p. 5696 - 5699
(2016/11/17)
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- Synthesis of new 3,3-dimethoxyazetidine-2-carboxylic acid derivatives
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Cyclization of γ-amino-α-bromocarboxylic esters resulted in an efficient synthesis of new 3,3-dimethoxyazetidine-2-carboxylates, that is, methyl N-t-butyl-3,3-dimethoxyazetidine-2-carboxylic ester and 3,3-dimethoxyazetidine-2-carboxylic acid, or 3-bromo-4
- Mangelinckx, Sven,Boeykens, Marc,Vliegen, Maarten,Van Der Eycken, Johan,De Kimpe, Norbert
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p. 525 - 529
(2007/10/03)
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- Synthesis of 4-alkyl-1-benzhydryl-2-(methoxymethyl)azetidin-3-ols by regio- and stereoselective alkylation of 1-benzhydryl-3-(N-alkyl)imino-2-(methoxymethyl)azetidine
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The regio- and stereoselective alkylation at the position C-4 of 1-alkyl-2-substituted azetidin-3-ones was investigated. Imination of 1-benzhydryl-2-methoxymethylazetidin-3-one, followed by alkylation under kinetic conditions and final hydrolysis of the imino group, gave 4-alkyl-1-benzhydryl-2-methoxymethylazetidin-3-ones in which the susbstituents at C-2 and C-4 had the cis stereochemistry. The reduction of the carbonyl group afforded the corresponding 4-alkyl-1-benzhydryl-2-methoxymethylazetidin-3-ols. The structure and the stereochemistry of the azetidinols were confirmed by single crystal X-ray diffraction analysis.
- Salgado, Antonio,Boeykens, Mark,Gauthier, Christine,Declercq, Jean-Paul,De Kimpe, Norbert
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p. 2763 - 2775
(2007/10/03)
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- Methyl (E)-4-chloro-3-methoxy-2-butenoate: An extremely versatile four carbon building block
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Methyl (E)-4-chloro-3-methoxy-2-butenoate (3a) is inexpensively prepared from methyl 4-chloroacetoacetate using thionyl chloride and methanol on an industrial scale. Many nucleophilic substitution reactions of chloride, which are impossible with the unpro
- Duc,McGarrity,Meul,Warm
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p. 391 - 394
(2007/10/02)
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- Novel benzopyranylpyrrolinone derivatives
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Compounds of the formula STR1 wherein: R1 is cyano or nitro; R2 and R3 are independently hydrogen or lower alkyl; and R4 is alkyl; alkenyl; optionally substituted phenyl or phenyl lower alkyl; --(CH2)
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- Process for the production of 4-alkoxy-2(5H) thiophenones
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Process for the production of 4-alkoxy-2(5H) thiophenones, which are suitable as intermediate products, i.e., for the production of highly pure thiotetronic acid.
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- Process for the production of 4-chloro-3-alkoxy-but-2E-enoic acid alkyl esters
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A process for the production of 4-chloro-3-alkoxy-but-2E-enoic acid alkyl esters starting from 4-chloroacetoacetic acid chloride by reaction with a dialkyl sulfite. The produced intermediate products are used as structural elements for, i.a., pharmaceutical agents.
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