- Synthetic Entry to Polyfunctionalized Molecules through the [3+2]-Cycloaddition of Thiocarbonyl Ylides
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Here we present a comprehensive study on the [3+2]-cycloaddition of thiocarbonyl ylides with a wide variety of alkenes and alkynes. The obtained dihydro- and tetrahydrothiophene products serve as exceptionally versatile intermediates providing access to thiophenes, dienes, dendralenes, and vic-quarternary carbon centers. The use of high-pressure conditions enables thermally unstable, sterically encumbered or moderately reactive substrates to undergo the cycloaddition under mild conditions, thereby increasing the yield by up to 58percent. In addition, we showcase its utility by the formal syntheses of the pharmaceuticals NGB 4420 and tenilapine.
- Habiger, Christoph,Haut, Franz-Lucas,Korber, Johannes Nepomuk,Müller, Thomas,Magauer, Thomas,Mayer, Peter,Speck, Klaus,Wurst, Klaus
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supporting information
(2019/09/06)
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- A rapid synthesis of lavendustin-mimetic small molecules by click fragment assembly
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Lavendustin-mimetic small molecules modifying the linker -CH 2-NH- with an 1,2,3-triazole ring have been synthesized via a click chemistry. Two pharmacophoric fragments of lavendustin were varied to investigate chemical space and the auxophoric -CH2-NH- was altered to an 1,2,3-triazole for rapid click conjugation. The small molecules were evaluated against HCT116 colon cancer and CCRF-CEM leukemia cell lines. Among 28 analogues, 3-phenylpropyl ester 26b inhibited CCRF-CEM leukemia cell growth with GI50 value of 0.9 μM.
- Yoon, Jieun,Ryu, Jae-Sang
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supporting information; experimental part
p. 3930 - 3935
(2010/08/20)
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- Pd-catalyzed domino synthesis of internal alkynes using triarylbismuths as multicoupling organometallic nucleophiles
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Figure presented The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1-alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.
- Rao, Maddali L. N.,Jadhav, Deepak N.,Dasgupta, Priyabrata
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supporting information; experimental part
p. 2048 - 2051
(2010/07/03)
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