- CeCl3-mediated addition of acetylenic bis-lithium salts to aldehydes and ketones: An efficient route to bis-substituted alkyne diols
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An efficient, chemoselective protocol to access propargylic diols via a CeCl3-mediated addition reaction is reported. Propargylic alcohols were transformed into the corresponding acetylenic bis-lithium salt intermediates, which react with aldehydes and ketones in the presence of dry CeCl3 to furnish the corresponding bis-substituted alkyne diols. This protocol does not involve protection-deprotection or transmetallation steps, and allows the use of poorly reactive or highly enolizable substrates.
- Princival, Jefferson Luiz,Ferreira, Jeiely Gomes
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supporting information
p. 3525 - 3528
(2017/10/06)
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- Synthesis and in vitro evaluation of (R), (S) and (R/S)-2-hexyne-1,4-diol, a natural product produced by fungus Clitocybe catinus, and related analogs as potential anticancer agents
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The search for natural products and related analogs as potential anticancer agents has seen a significant growth worldwide. Since small sized propargylic diols can be found in nature and chemically synthesized, their evaluation against cancer cells has been of great interest, being a topic of relevance to be investigated. For this purpose, a scalable approach aiming at the synthesis of several propargylic diols and their bioactivity against seven tumor cell lines were evaluated. Interestingly, when the compound 1a, a natural product produced by fungus Clitocybe catinus, was tested in its racemic mixture a more effective activity was observed if compared when enantiopure R-1a or S-1a were tested separately.
- Princival, Iza Mirela R.G.,Ferreira, Jeiely G.,Silva, Teresinha G.,Aguiar, Jaciana S.,Princival, Jefferson L.
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supporting information
p. 2839 - 2842
(2016/06/09)
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- Regiocontrolled Formation of 4,5-Dihydro-3(2H)-furanones from 2-Butyne-1,4-diol Derivatives. Synthesis of Bullatenone and Geiparvarin
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Two new methods for selective hydration of 1,1,4-trisubstituted 2-butyne-1,4-diols (1) to give 4,5-dihydro-3(2H)-furanone derivatives are reported.The first involves selective monoacetylation of the less hindered hydroxyl group of 1 followed by Ag(I)-cata
- Saimoto, Hiroyuki,Hiyama, Tamejiro,Nozaki, Hitosi
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p. 3078 - 3087
(2007/10/02)
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