927-57-1Relevant articles and documents
Enzymatic kinetic resolution of internal propargylic diols. Part I: A new approach for the synthesis of (S)-pent-2-yn-1,4-diol, a natural product from Clitocybe catinus
Ferreira, Jeiely G.,Princival, Cleverson R.,Oliveira, Dyego M.,Nascimento, Renata X.,Princival, Jefferson L.
, p. 6458 - 6462 (2015)
Internal bis-substituted propargylic diols were subjected to enzymatic kinetic resolution promoted by CAL-B. Employing a two round sequence EKR, mono- and bis-acetoxy propargylic products were obtained in a high enantiomeric ratio (E > 200). The efficiently resolved chiral 8b was applied in a concise synthesis of (S)-1b, an optically active natural product produced by fungi Clitocybe catinus.
CeCl3-mediated addition of acetylenic bis-lithium salts to aldehydes and ketones: An efficient route to bis-substituted alkyne diols
Princival, Jefferson Luiz,Ferreira, Jeiely Gomes
supporting information, p. 3525 - 3528 (2017/10/06)
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.
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
Princival, Iza Mirela R.G.,Ferreira, Jeiely G.,Silva, Teresinha G.,Aguiar, Jaciana S.,Princival, Jefferson L.
supporting information, p. 2839 - 2842 (2016/06/09)
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.
