98441-94-2Relevant academic research and scientific papers
Total synthesis of (±)-hedychilactone B: Stepwise allenoate diene cycloaddition to prepare trimethyldecalin systems
Jung, Michael E.,Murakami, Masayuki
, p. 461 - 463 (2007)
The total synthesis of the diterpene hedychilactone B 1 is reported. The exo adduct 4x, the major product of the stepwise [4+2] cycloaddition of the diene 2 and the allenoate 3, has been converted into 1 via 7 steps, among them a key nonconjugative hydrol
A modular and scalable one-pot synthesis of polysubstituted furans
Fournier, Jeremy,Arseniyadis, Stellios,Cossy, Janine
supporting information; experimental part, p. 7562 - 7566 (2012/10/18)
One four all: Allyl dienol carbonates can be readily converted into diversely substituted furans by a one-pot four-step sequence featuring a palladium-catalyzed decarboxylative allylic alkylation, a microwave-mediated Cope rearrangement, a nucleophilic addition, and a dehydration reaction (see scheme). The protocol is operationally simple, highly flexible, and provides di-, tri-, and tetrasubstituted furans starting from readily available materials. Copyright
Custom synthesis of substituted butenolides, dihydropyranones, and α-E-alkylidenelactones via alkenylalumination
Veeraraghavan Ramachandran,Pratihar, Debarshi,Garner, Garrett,China Raju
, p. 4985 - 4988 (2011/10/08)
Alkenylalumination of aldehydes with [α-(ethoxycarbonyl)-β-(t- butyldimethylsilyloxyalkyl)alkenyl]diisobutylaluminum provides the corresponding α-Z-alkylidene-β′-hydroxy esters, which upon protection and treatment with trifluoroacetic acid lactonizes to f
Total Synthesis of the ent-Clerodane Diterpenoids (+/-)-Isolinaridiol and (+/-)-Isolinaridiol Diacetate
Piers, Edward,Wai, John S. M.
, p. 1245 - 1247 (2007/10/02)
A previously described mixture of bicyclodecanecarbonitriles was converted, via a nine-step sequence of reactions, into (+/-)-isolinaridiol (3), which was readily transformed into the corresponding diacetate (2).
Stereoselective Synthesis of (E)- or (Z)-α-Alkylidene-γ-butyrolactone from γ-Butyrolactone and Bis Disulfide and Mechanistic Studies of the Effect of Metal Complexes on the Stereoselection
Matsui, Syuichi
, p. 1853 - 1866 (2007/10/02)
Treatment of γ-butyrolactone with bis disulfide in presence of 2.2. equiv of lithium diisopropylamide (LDA) produced lithium enolate of O-ethyl S-(tetrahydro-2-oxo-3-furanyl) dithiocarbonate, which reacted with an aldehyde to afford exclusively (E)-α-alkylidene-γ-butyrolactone.Interestingly, when the reaction was quenched below -20 deg C or when it was carried out in the presence of metal complex such as zinc chloride, copper(I) iodide, or tributyltin chloride, (Z)-α-alkylidene-γ-butyrolactone was obtained as the major product.The stereoselectivity of this reaction was sensitive to the reaction temperature and the metal cation employed.
New Methods for Stereoselective Synthesis of α-Alkylidene-γ-butyrolactones Using Monoanion of O-Ethyl S-(Tetrahydro-2-oxo-3-furanyl) Thiocarbonate and Dianion of α-Mercapto-γ-butyrolactone
Tanaka, Kazuhiko,Uneme, Hideki,Yamagishi, Nobuyuki,Tanikaga, Rikuhei,Kaji, Aritsune
, p. 2910 - 2916 (2007/10/02)
The lithium enolates of O-ethyl S-(tetrahydro-2-oxo-3-furanyl) dithiocarbonate and thiocarbonate were found to be efficient reagents for the stereoselective synthesis of α-alkylidene-γ-butyrolactones from carbonyl compounds.The dianion of α-mercapto-γ-butyrolactone was successfully generated by treatment of α-mercapto-γ-butyrolactone with 2.2 equivalents of lithium diisopropylamide in the presence of N,N,N',N'-tetramethylethylenediamine at -78 deg C in THF.The dianion thus formed has been utilized for the efficient and stereoselective synthesis of α-alkylidene-γ-butyrolactones from carbonyl compounds.
