98126-46-6Relevant academic research and scientific papers
Electrooxidative coupling of furans and silyl enol ethers: Application to the synthesis of annulated furans
Sperry, Jeffrey B.,Whitehead, Christopher R.,Ghiviriga, Ion,Walczak, Ryan M.,Wright, Dennis L.
, p. 3726 - 3734 (2007/10/03)
The preparation of annulated furan systems as key synthetic intermediates through the application of a two-step annulation involving an electrochemical ring closure between a furan and a silyl enol ether has been studied. The reaction was shown to be quite general for the formation of six-membered rings in good yields and was tolerant of a variety of different functional groups. The ring closure was highly stereoselective, leading to the formation of cis-fused systems. Cyclic voltammetry and probe molecules were used to gain mechanistic insight into the reaction. These studies suggested that the key ring closure involved an initial oxidation of the silyl enol ether to a radical cation followed by a furan-terminated cyclization.
A new route to 2,7- and 7-functionalized labdanes
Hersel, Ulrich,Steck, Melanie,Seifert, Karlheinz
, p. 1609 - 1615 (2007/10/03)
A new route for the synthesis of 2,7- and 7-functionalized labdanes starts from (R)-carvone (1). 11-Nordrim-7-en-9-one (15) is an appropriate starting material for the total synthesis of hispanone (21), a biologically active furolabdane isolated from the
The first enantioselective synthesis of (-)-microcionin 2
Potvin, Steeves,Canonne, Persephone
, p. 2821 - 2824 (2007/10/03)
An approach known to give regiospecific and stereospecific reactions has been applied to the enantioselective synthesis of the natural (-)-microcionin 2 (1), a prototype of trans relationship of the methyl groups on the furanosesquiterpenes.
Furans in Synthesis. 5. Furan-Terminated Cationic Cyclizations in the Preparation of Fused, Spirocyclic and Bridged Ring Systems. An Application to the Synthesis of Nakafuran 9
Tanis, Steven P.,Herrinton, Paul M.
, p. 3988 - 3996 (2007/10/02)
The title compounds 36-42 and nakafuran 9 (43) were prepared by furan-terminated cationic cyclizations.The cyclization substrates, allylic alcohols 16, 17, 25, 26, 33, and 34, and the derived enone 19 were prepared by CuCN moderated SN2' addition of Grignard reagents derived from 2-(3-furyl)-1-bromoethane (12) and 3-(3-furyl)-1-bromopropane (13) to vinyl epoxides 14 and 22 and epoxy enol ether 21.Treatment of substrate allylic alcohols with a two-phase mixture of HCO2H and cyclohexane resulted in facile cyclization when the forming ring was six or seven membered.Enone closures proceeded only when a six-membered ring was produced or in the case of enone 48 which leads to nakafuran 9 (43).
