22697-33-2Relevant academic research and scientific papers
A convenient route to 2,6-dialkyl-2,3-dihydro-4H-pyran-4-ones via oxidative cleavage of protected 1-(2-oxoalkyl)-cyclopropanols. Synthesis of (±)-hepialone and its natural congener
Astashko, Dmitry A.,Tyvorskii, Vladimir I.
, p. 4792 - 4794 (2011)
An efficient strategy for the synthesis of 2,6-dialkyl-2,3-dihydro-4H- pyran-4-ones has been developed, the key steps of which are oxidative cleavage of the three-membered rings of 1-(2-oxoalkyl)-cyclopropanols and acid-promoted cyclization of the resulting β-hydroxyketones.
Enantioselective Synthesis of Spiro Ethers and Spiro Ketals via Photoaddition of Dihydro-4-pyrones to Chiral 1,3-Dioxin-4-ones 1
Haddad, Nizar,Rukhman, Igor,Abramovich, Zehavit
, p. 7629 - 7636 (2007/10/03)
A versatile and highly stereoselective synthesis of spiro ethers and spiro ketals is presented. The key step in the developed synthetic sequence is based on diastereoselective intramolecular photoaddition of dihydro-4-pyrones to chiral 1,3-dioxin-4-ones. Subsequent fragmentation of the produced four-membered ring provides spiro ether structures. The spiro ethers can be transformed to their corresponding spiro ketals, with retention of configuration at the spiro center, via Baeyer-Villager oxidation. The configuration of the spiro center is defined by the facial selectivity at the photocycloaddition step. Two examples of complete stereofacial selectivity were achieved. The unique and important application of the developed sequence was demonstrated in enantioselective synthesis of a less thermodynamically stable spiro ketal 43.
CHEMISTRY AND SYNTHETIC POTENTIAL OF THE REACTIONS OF 3-CHLORO-1,3-ALKADIEN-5-ONES WITH SODIUM METHOXIDE
Melikyan, G. G.,Tosunyan, A. A.,Babayan, E. V.,Atanesyan, K. A.,Badanyan, Sh. O.
, p. 1802 - 1807 (2007/10/02)
The reactions of (E)- and (Z)-3-chloro-1,3-alkadien-5-ones with sodium methoxide were investigated.The reactions from a process of successive interaction of the substrates with three molecules of the reagent with alternation of the recipient atom (C3-C1-C3).The introduction of a methyl group at position 2 of the substrate molecule gives rise to regioselective reaction at the C3-C4 double bond.
HYDRATION OF ALLENYLACETYLENIC ALCOHOLS - NEW ROUTE TO 6-METHYL-2,3-DIHYDRO-4-PYRANONES
Khrimyan, A. P.,Karapetyan, A. V.,Badanyan, Sh. O.
, p. 495 - 498 (2007/10/02)
The mercuric sulfate-catalyzed acidic hydration of allenylacetylenic alcohols leads to 6-methyl-2,3-dihydro-4-pyranones - products of cyclization of unsaturated β-diketones.In the case of 1-(3,4-pentadien-1-ynyl)cyclohexanol 2-(1-cyclohexenyl)-5-methylfuran is formed in addition to the corresponding dihydropyranone.
