127308-75-2Relevant academic research and scientific papers
Synthesis of (±) cis-substituted cyclohexenyl and cyclohexanyl nucleosides via a double Mitsunobu-type reaction
Barral, Karine,Halfon, Philippe,Pèpe, Gérard,Camplo, Michel
, p. 81 - 84 (2002)
This letter describes the synthesis of (±) cis-substituted cyclohexenyl and cyclohexanyl nucleosides. The synthesis of cis isomers was successfully achieved by the use of two consecutive Mitsunobu reactions involving an inversion of configuration and a sugar-base condensation.
Palladium-Catalyzed Allylic Alkylation of 2-Aryl-1,3-Dithianes, an Umpolung Synthesis of β,γ-Unsaturated Ketones
Trongsiriwat, Nisalak,Li, Minyan,Pascual-Escudero, Ana,Yucel, Baris,Walsh, Patrick J.
supporting information, p. 502 - 509 (2018/12/11)
Palladium-catalyzed allylic alkylation of 2-aryl-1,3-dithianes at room temperature is described. A variety of cyclic and acyclic electrophiles successfully coupled with in-situ generated 2-sodio-1,3-dithiane nucleophiles to afford the allylated products in good to excellent yields (25 examples). Deprotection of these products leads to valuable β,γ-unsaturated ketones. Direct synthesis of such β,γ-unsaturated ketones via a one-pot allylation-oxidation protocol is also presented. Investigation into the stereochemistry of the allylation reaction revealed that the 2-sodio-1,3-dithiane nucleophile behaves as a “soft” nucleophile, which underwent external attack on the π-allyl palladium complex to provide retention of stereochemistry (double inversion pathway). Additionally, the utility of this method was demonstrated through a sequential one-pot allylation-Heck cyclization to produce asterogynin derivatives, which are important bioactive compounds in medicinal chemistry. (Figure presented.).
Catalytic sp3–sp3Functionalisation of Sulfonamides: Late-Stage Modification of Drug-Like Molecules
Abdulla, Othman,Clayton, Adam D.,Faulkner, Robert A.,Gill, Duncan M.,Rice, Craig R.,Walton, Scarlett M.,Sweeney, Joseph B.
supporting information, p. 1494 - 1497 (2017/02/10)
A new application of Pd-catalysed allylation is reported that enables the synthesis of a range of branched sp3-functionalised sulfonamides, a compound class for which few reported methods exist. By reacting benzyl sulfonamides with allylic acetates in the presence of Pd0catalysts and base at room temperature, direct allylation was efficiently performed, yielding products that are analogues of structural motifs seen in biologically active small molecules. The reaction was performed under mild conditions and could be applied to nanomolar sigma-receptor binders, thus enabling a late-stage functionalisation and efficient expansion of drug-like chemical space.
A-ring hydroxymethyl 19-nor analogs of the natural hormone 1α,25-dihydroxyvitamin D3: Synthesis and preliminary biological evaluation
Hatcher, Mark A.,Peleg, Sara,Dolan, Patrick,Kensler, Thomas W.,Sarjeant, Amy,Posner, Gary H.
, p. 3964 - 3976 (2007/10/03)
A series 5-8 of 1- and 3-CH2OH 19-nor analogs of the hormone calcitriol (1) has been prepared. Surprisingly, 19-nor 1α-CH2OH analog 5a is more antiproliferative at 100 nM concentration than the corresponding regioisomeric analog 6a w
Synthesis and antiviral evaluation of cis-substituted cyclohexenyl and cyclohexanyl nucleosides
Barral, Karine,Courcambeck, Jér?me,Pèpe, Gérard,Balzarini, Jan,Neyts, Johan,De Clercq, Erik,Camplo, Michel
, p. 450 - 456 (2007/10/03)
Starting from commercially available (rac)-3-cyclohexene-1-carboxylic acid, a series of purine and pyrimidine cis-substituted cyclohexenyl and cyclohexanyl nucleosides were synthesized through a key Mitsunobu reaction. Antiviral evaluations were performed
Practical syntheses of enantiopure carbasugars: Carba-β-altrose, carba-β-mannose, carba-β-idose, and carba-β-talose derivatives
Yu, Seok-Ho,Chung, Sung-Kee
, p. 581 - 584 (2007/10/03)
D and L forms of carba-β-altrose 8, carba-β-mannose 10a, carba-β-idose 12, carba-β-talose 14 derivatives were prepared from (±)-3-cyclohexene-1-carboxylic acid 1. Homochiral diol compounds D-5a and L-5a, which were prepared from 1 via enzyme resolution of
Efficient Preparation of Intermediates Corresponding to C22-C27 and C28-C34 of FK-506
Linde, II Robert G.,Egbertson, Melissa,Coleman, Robert S.,Jones, A. Brian,Danishefsky, Samuel J.
, p. 2771 - 2776 (2007/10/02)
Efficient large-scale preparations of aldehyde 2 and sulfone 3 representing the C22-C27 and C28-C34 potions of the immunosuppressant FK-506 (1) are descibed.
FK-506 SYNHETIC STUDIES. 3. AN EFFICIENT ASYMMETRIC SYNTHESIS OF THE C(24)-C(34) FRAGMENT OF FK-506, FR-900520, AND FR-900523
Smith, Amos B. III.,Hale, Karl J.,Laakso, Leif M.,Chen, Kwunmin,Riera, Antoni
, p. 6963 - 6966 (2007/10/02)
An efficient asymmetric synthesis of the C(24)-C(34) fragment of the FK-506 family of immunosuppressants has been achieved.
