41143-12-8Relevant articles and documents
STUDIES ON THE SYNTHESIS OF GLOEOSPORONE - SYNTHESIS OF THE PROPOSED 2,8-DISUBSTITUED OXOCANE STRUCTURE
Carling, Robert W.,Holmes, Andrew B.
, p. 6133 - 6136 (1986)
Gloeosporone is neither the cis- nor the trans-2,8-disubstituted oxocane (1) nor its tautomer (2) whose total syntheses are described in this Letter.
Practical synthesis of hex-5-ynoic acid from cyclohexanone
Starostin,Lapitskaya,Ignatenko,Pivnitsky,Nikishin
, p. 81 - 84 (2000)
Hex-5-ynoic acid, a multipurpose synthon, was synthesized in three steps starting from cyclohexanone by bromination-dehydrobromination of the intermediate hex-5-enoic acid.
Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes
Liu, Mingyu,Tang, Tianhua,Apolinar, Omar,Matsuura, Rei,Busacca, Carl A.,Qu, Bo,Fandrick, Daniel R.,Zatolochnaya, Olga V.,Senanayake, Chris H.,Song, Jinhua J.,Engle, Keary M.
supporting information, p. 3881 - 3888 (2021/04/06)
Selective carbon-carbon (C-C) bond formation in chemical synthesis generally requires prefunctionalized building blocks. However, the requisite prefunctionalization steps undermine the overall efficiency of synthetic sequences that rely on such reactions, which is particularly problematic in large-scale applications, such as in the commercial production of pharmaceuticals. Herein, we describe a selective and catalytic method for synthesizing 1,3-enynes without prefunctionalized building blocks. In this transformation several classes of unactivated internal acceptor alkynes can be coupled with terminal donor alkynes to deliver 1,3-enynes in a highly regio- and stereoselective manner. The scope of compatible acceptor alkynes includes propargyl alcohols, (homo)propargyl amine derivatives, and (homo)propargyl carboxamides. This method is facilitated by a tailored P,N-ligand that enables regioselective addition and suppresses secondary E/Z-isomerization of the product. The reaction is scalable and can operate effectively with as low as 0.5 mol % catalyst loading. The products are versatile intermediates that can participate in various downstream transformations. We also present preliminary mechanistic experiments that are consistent with a redox-neutral Pd(II) catalytic cycle.
Gold(I)-Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco-Friendly Synthesis of γ-, δ- and ?-Lactones
Gasperini, Danila,Maggi, Lorenzo,Dupuy, Stéphanie,Veenboer, Richard M. P.,Cordes, David B.,Slawin, Alexandra M. Z.,Nolan, Steven P.
supporting information, p. 3857 - 3862 (2016/12/16)
The improved synthesis of γ-, δ- and ?-lactones using a dinuclear N-heterocyclic carbene (NHC)-gold(I) catalyst is reported. This solvent-free process provides access to γ- and δ-lactones in high regio- and stereoselectivity. Reactions were performed at l
