63305-65-7Relevant academic research and scientific papers
Amide analogs of antifungal dioxane-triazole derivatives: Synthesis and in vitro activities
Uchida, Takuya,Kagoshima, Yoshiko,Konosu, Toshiyuki
scheme or table, p. 2013 - 2017 (2009/11/30)
A new series of triazole compounds possessing an amide-part were efficiently synthesized and their in vitro antifungal activities were investigated. The amide analogs showed excellent in vitro activity against Candida, Cryptococcus and Aspergillus species
Formal convergent synthesis of ivermectin aglycone - A synthetic approach to the C10-C25 subunit of avermectins 2b
Henryon, Vivien,Ferezou, Jean-Pierre
experimental part, p. 3477 - 3487 (2010/03/02)
A convergent, two-fragment synthesis of the C10-C25 northern moiety of avermectins has been developed. Along with our previous work in this area, the present contribution represents a formal synthesis of Ivermectin aglycone. Furthermore, according to a strategy leading to non y-pyranone adducts from, the condensation reaction between acetylacetone dianion and convenient aldehydes, 23-hydroxylated C10-C25 northern building blocks required for the synthesis of the avermectins series 2b were prepared. Subsequent unexpected kinetically favored unnatural (215)-spiro isomers were obtained under mild cyclization conditions.
FeCl3ATMSCl: An effective catalytic system for the conjugate addition of sodium p-toluenesulfinate to αβ-enones
Sreedhar,Reddy, M. Amamath,Reddy, P. Surendra
experimental part, p. 1949 - 1952 (2009/04/10)
A new protocol for the β-sulfonation of αβ-unsaturated carbonyl compounds is described. The method employs FeCl3 as catalyst and TMSC1 as additive for conjugate addition of sodiump-toluenesulfinate to enones.
Highly efficient two-step synthesis of C-sp3-centered geminal diiodides
Cloarec, Jean-Manuel,Charette, Andre B.
, p. 4731 - 4734 (2007/10/03)
(Chemical Equation Presented) Trisubstituted gem-diiodoalkenes of functionalized chains are efficiently reduced to the corresponding terminal geminal diiodides in high yields upon treatment with the diazene precursor, diethyl 4-(hydrazinosulfonyl)-benzyl phosphonate.
Total synthesis of avermectins Part 2: Enantioselective synthesis of the C10-C25 northern fragment and final steps for the construction of the 22,23-dihydroavermectin B1b aglycone
Ferezou, Jean-Pierre,Julia, Marc,Li, Yun,Liu Lu Wei,Pancrazi, Ange
, p. 428 - 452 (2007/10/02)
The total synthesis of the aglycone of 22,23-dihydroavermectin B1b involves a retrosynthetic two building-blocks approach.A Stille Pd(0) catalyzed cross-coupling reaction is carried out between a northern C10-C25 E-vinylstannane and a southern C1-C9 vinyl iodide.The final steps include successive removal of the carboxyl β-(trimethylsilyl)ethyl protecting group of the intermediate secoester, macrolactonization under Yonemitsu's conditions and removal of the 5-O-TBS protecting group.These last steps have been carried out with the aid of a relay study from commercial Ivermectin; a macrolactone opening reaction of the aglycone in the presence of Ti(OiPr)4 has been developed where the crucial Δ3,4 double bond as well as the configuration at C-2 were totally preserved. - Key words: avermectin / spiroketal / diastereoselection / aldolization / sulfone / homoaldolization / Hoppe reaction / hydrostannylation / palladium Stille coupling / titanium isopropoxide / transesterification / macrolactone / total synthesis
Lithiated 3-Tosylpropanal and 4-Tosyl-2-butanone Dimethyl Acetals as β-Acylvinyl Anion Equivalents for the Synthesis of Unsaturated 1,4-Dicarbonyl Compound and α,β-Butenolides
Bonete, Pedro,Najera, Carmen
, p. 2763 - 2776 (2007/10/02)
The lithiation of 1,1-dimethoxy-3-tosyllpropane (7a) and 2,2-dimethoxy-4-tosylbutane (7b) followed by reaction with acyl chlorides affords, after p-toluenesulfinic acid elimination, ene-1,4-dicarbonyl compounds in a stereoselective manner.In the case of compound 7a, derived from acrolein, sequential monolithiation and reaction with carbonyl compounds give cyclic acetals, which after oxidation and elimination of p-toluenesulfinic acid are transformed into α,β-butenolides.
"Syn-Effect" in the Conversion of (E)-Vinylic Sulfones to the Corresponding Allylic Sulfones
Hirata, Takaki,Sasada, Yoshihiro,Ohtani, Takashi,Asada, Takahiro,Kinoshita, Hideki,et al.
, p. 75 - 96 (2007/10/02)
It was found that (E)-vinylic sulfones preferentially afford (Z)-allylic sulfones as kinetically-controlled products by treatment with a base under mild conditions, while (Z)-vinylic sulfones give (E)-allylic sulfones.Such stereochemical relationship was
