119480-92-1Relevant academic research and scientific papers
Synthesis and Molecular Editing of Callyspongiolide, Part 1: The Alkyne Metathesis/trans-Reduction Strategy
Mata, Guillaume,W?lfl, Bernhard,Fürstner, Alois
supporting information, p. 246 - 254 (2019/01/04)
A path-scouting investigation into the highly cytotoxic marine macrolide callyspongiolide is reported that capitalizes on the selective formation of the C10?C11 alkene site. While the closure of the macrocycle by ring closing alkyne metathesis (RCAM) with
[4 + 2]-Annulations of chiral organosilanes: Application to the total synthesis of leucascandrolide A
Su, Qibin,Dakin, Les A.,Panek, James S.
, p. 2 - 24 (2007/10/03)
Complete details of an asymmetric synthesis of leucascandrolide A (1) are described. The synthesis highlights the use of two diastereoselective [4 + 2]-annulations for the assembly of the functionalized bispyranyl macrolide 3. An efficient assembly and un
Reactions of phenyldimethylsilyllithium with β-N,N- dimethylaminoenones: A convenient synthesis of β-dimethyl(phenyl) silylacrylic acid and its derivatives
Fleming, Ian,Marangon, Elena,Roni, Chiara,Russell, Matthew G.,Chamudis, Sandra Taliansky
, p. 325 - 332 (2007/10/03)
Phenyldimethylsilyllithium reacted with 5,5-dimethyl-3-(N,N,-dimethylamino) cyclohex-2-enone (7), 3-(E)-N,N-dimethylaminopropenal (11), and 4-N,N-dimethylaminobut-3-en-2-one (13) to give the corresponding β-silyl-α,β-unsaturated carbonyl compounds 8, 12, and 14, in which the dimethylamino group has been displaced by the phenyldimethylsilyl group. Phenyldimethylsilyllithium reacted with ethyl β-N,N- dimethylaminopropenoate (15) by conjugate addition, but, in contrast to the ketones 7 and 13 and the aldehyde 11, the intermediate enolate 16 was C-protonated in the aqueous work-up to give ethyl 3-N,N-dimethylamino-3- dimethyl(phenyl)silylpropanoate (17). When the enolate 16 was instead given a mysteriously brief treatment with methyl iodide before work-up, the product was ethyl 3-(E)-dimethy(phenyl)silylpropenoate (18). Phenyllithium and methyllithium also added conjugatively to ethyl β-N,N-dimethylaminoacrylate (15) but, in contrast to the silyl case, the intermediate enolate 22 reacted unexceptionally with methyl iodide to give the products 25 and 26 of stereoselective C-methylation. This synthesis of the ester 18 was used to synthesize the Oppolzer sultam derivative 30.
Reactions of phenyldimethylsilyllithium with β-N,N-dimethylaminoenones
Fleming, Ian,Marangon, Elena,Roni, Chiara,Russell, Matthew G.,Chamudis, Sandra Taliansky
, p. 200 - 201 (2007/10/03)
Phenyldimethylsilyllithium reacts with the β-N,N-dimethylaminoenones 1 and 7, with the enal 5, and with ethyl β-N,N-dimethylaminoacrylate 9 to give the corresponding α,β-unsaturated carbonyl compounds with a β-phenyldimethylsilyl group, but in the last ca
Diastereoselectivity in the Preparation of β-Silyl Esters from αβ-Unsaturated Esters and Amides Attachhed to Chiral Auxiliaries
Fleming, Ian,Kindon, Nicolas D.
, p. 303 - 316 (2007/10/02)
The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides 1 of various known chiral auxiliaries, a-e, is diastereoselective.The sense of diastereoselectivity of silyl-cuprate addition to the esters 1b-d, 8 and 9 is different from established precedent based on carbon-cuprates, but is normal for silyl-cuprate addition to the amide 1a, the imines 1e and 21, and the oxazolidine 6.The chiral auxiliary e gives the best results of those tested, and the silicon-containing group can be removed from the chiral auxiliary using alkoxide ion in aprotic media, making available β-silyl esters 27-29 of high enantiomeric excess, with recovery of the chiral auxiliary 30.
Catalytic Asymmetric Addition of Polyfunctional Dialkylzincs to β-Stannylated and β-Silylated Unsaturated Aldehydes
Ostwald, Roswitha,Chavant, Pierre-Yves,Stadtmueller, Heinz,Knochel, Paul
, p. 4143 - 4153 (2007/10/02)
The addition of functionalized dialkylzincs to readily available β-stannylated or β-silylated unsaturated aldehydes in the presence of a catalytic amount of (1R,2R)-1,2-bis(trifluorosulfonamido)cyclohexane (8 mol percent) provides chiral allylic alcohols
Allylsilanes in organic synthesis; an approach to the stereoselective synthesis of units for natural product synthesis
Murphy,Procter
, p. 1059 - 1062 (2007/10/02)
Allylsilane chemistry been used in the stereoselective syntheses of (13), a system which could serve in the synthesis of several polyketide natural products including tiransamycin.
