40844-09-5Relevant academic research and scientific papers
Total syntheses of the resorcylic acid lactones paecilomycin F and cochliomycin C using an intramolecular loh-type α-allylation reaction for macrolide formation
Ma, Xiang,Bolte, Benoit,Banwell, Martin G.,Willis, Anthony C.
supporting information, p. 4226 - 4229 (2016/09/09)
Subjection of the resorcylic ester 16 to a Nozaki-Hiyama-Kishi reaction afforded the 12-membered lactone 17, while treatment of it under the Loh-type α-allylation conditions using indium metal gave the isomeric, 14-membered macrolide 18. Compound 18 was readily elaborated to the resorcylic acid lactone type natural products paecilomycin F and cochliomycin C.
Total Synthesis of Tetraketide and Cryptorigidifoliol i via a Sequential Allylation Strategy
Padhi, Birakishore,Reddy, G. Sudhakar,Mohapatra, Debendra K.
, p. 2788 - 2796 (2016/12/06)
A unified and efficient synthetic route for both tetraketide (1) and cryptorigidifoliol I (2) has been devised successfully from commercially available starting materials in 11 and 17 steps, with 16% and 11% overall yields, respectively. Highlights of the syntheses involved sequential Lewis acid-catalyzed highly regio- and diastereoselective allylations and intramolecular Mitsunobu lactonization.
Lewis acid-promoted addition of 1,3-bis(silyl)propenes to aldehydes: A route to 1,3-dienes
Borg, Tessie,Tuzina, Pavel,Somfai, Peter
experimental part, p. 8070 - 8075 (2011/11/28)
The Lewis acid-promoted addition of 1,3-bis(silyl)-propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.
Isomerisation of (E)-2-tetrahydrofurylidenealkanecarboxylic esters and amides into their (Z) isomers by chelation control with metallated bases or Lewis acids
Hanquet, Gilles,Salom-Roig, Xavier J.,Lemeitour, Sonia,Solladie, Guy
, p. 2112 - 2119 (2007/10/03)
2-(2-Tetrahydrofurylidene)propionates, usually obtained only in the more stable (E) configuration 1, were efficiently isomerised into their (Z) isomers 2 by use of Lewis acids or metallated bases. The (E)/(Z) isomerisation was governed by different factors (type of chelating agent, nature and steric demand of the α, β-unsaturated group). We demonstrated that judicious selection of the α, β-unsaturated group, in combination with the chelating agent, afforded yields of up to 95% with either LDA [R = N(Me)2, tBu] or MgBr2 and ZnI2 (R = OBn), and that the reaction was also influenced by 1,3-allylic strains. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
SYNTHESIS OF TRIFLUOROMETHYLATED TETRAHYDROPYRANS FROM ENE REACTION PRODUCTS OF TRIFLUOROMETHYL KETONES: sYNTHESIS OF FLUORINE ANALOGS OF SESQUITERPENE
Nagai, Takabumi,Ohtsuka, Hiroshi,Koyama, Mayumi,Ando, Akira,Miki, Takuichi,Kumadaki, Itsumaro
, p. 51 - 54 (2007/10/02)
As the extension of the ene reaction of trifluoromethyl ketones, α-trifluoromethylated tetrahydropyrans, including fluorine analogs of sesquiterpenes, were synthesized from trifluoromethylated homoallyl alcohols, the products of the ene reaction.
[3+3] Annulation by sequential two electron and one electron allylation
Ward, Dale E.,Kaller, Brian F.
, p. 843 - 846 (2007/10/02)
3-phenylthio-2-(trimethylsilymethyl)propene is a convenient conjunctive reagent for the preparation of methylenecyclohexanes via a [3+3] annulation. The trimethylsilyl group facilitates the Lewis acid catalyzed allylation of an aldehyde or acetal while the phenylthio group directs a 6-endo-trig radical cyclization reaction.
REACTION OF DIANIONS DERIVED FROM β-KETOESTERS WITH EPOXIDES - UTILITY IN THE PREPARATION OF SYNTHETICALLY USEFUL TETRAHYDROFURANS.
Lygo, Barry,O'connor, Norval,Wilson, Peter R.
, p. 6881 - 6888 (2007/10/02)
Presented here are several examples which demonstrate that ether substituents α- or β- to an epoxide ring can be tolerated in the ring-opening reaction with β-keto ester dianions.Subsequent acid-promoted cyclisation of the γ-hydroxy β-ketoesters then leads to synthetically useful tetrahydrofurans, as demonstrated by application of this approach to the preparation of (+/-)-methyl nonactate and (+/-)-methyl 8-epi-nonactate.
STEREOSELECTIVE SYNTHESIS OF (+/-)-METHYL NONACTATE AND (+/-)-METHYL 8-epi-NONACTATE.
Lygo, Barry,O'Connor, Norval
, p. 3597 - 3600 (2007/10/02)
(+/-)-Methyl nonactate (2) and (+/-)-methyl 8epi-nonactate (3), synthetic precursors to the antibiotic nonactin have been synthesised, employing the reaction of substituted epoxides with dianions derived from β-ketoesters as the key carbon-carbon bond-for
Chiral Building Units from Carbohydrates, VIII. - Syntheses of the Four Isomeric 1,3-Dimethyl-2,9-dioxabicyclononanes
Redlich, Hartmut,Schneider, Bernd,Hoffmann, Reinhard W.,Geueke, Karl-Josef
, p. 393 - 411 (2007/10/02)
Starting from different compounds, the syntheses of the four isomeric bicyclic acetals 17, 32, 36, and 40 - the title compounds - are described.One of these compounds is supposed to direct the attack of the striped ambrosia beetle Trypodendron lineatum Ol
