209802-54-0Relevant articles and documents
A facile synthesis of CD45 protein tyrosine phosphatase inhibitor marine natural product pulchellalactam
Mangaleswaran, Sivaprakasam,Argade, Narshinha P.
, p. 1560 - 1562 (2004)
A facile five-step route to the naturally occurring CD45 protein tyrosine phosphatase inhibitor, (Z)-pulchellalactam, with 64% overall yield has been demonstrated starting from citraconimide (5) via regioselective NaBH4 reduction, catalytic hydrogenation, resin-catalyzed dehydration, W-BOC protection, and stereoselective condensation pathway.
A novel short approach to (Z)-pulchellalactam through transition-metal- catalyzed atom-transfer radical cyclization of 1-isopropylprop-2-enyl dichloroacetate
Felluga, Fulvia,Ghelfi, Franco,Pagnoni, Ugo M.,Parsons, Andrew F.,Pattarozzi, Mariella,Roncaglia, Fabrizio,Valentin, Ennio
, p. 1882 - 1886 (2007)
A new, five-step route to (Z)-pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor, is presented. Key steps are the copper(I) chloride-bipyridyl catalyzed atom-transfer radical cyclization of an appropriate allyl α,α-dichloroacetate and the subsequent dehydrochlorination/ prototropic rearrangement of the resulting dichlorolactone. Georg Thieme Verlag Stuttgart.
Total synthesis of pulchellalactam via an RCM strategy
Chavan, Subhash P.,Pathak, Ashok B.,Dhawane, Abasaheb N.,Kalkote
, p. 1503 - 1510 (2007)
Total synthesis of (Z) pulchellalactam, a CD protein tyrosine phosphatase inhibitor, from commercially available methallyl chloride employing ring-closure metathesis (RCM) as a key step is described. Copyright Taylor & Francis Group, LLC.
Convenient synthesis of pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor from the marine fungus Corollospora pulchella, and its related compounds
Bessho, Jun-Ichiro,Shimotsu, Yasuhiko,Mizumoto, Sachiko,Mase, Nobuyuki,Yoda, Hidemi,Takabe, Kunihiko
, p. 1013 - 1016 (2004)
Convenient synthesis of pulchellalactam (1a) and its related compounds was accomplished. Total yields of (Z)-pulchellalactam and (E)-pulchellalactam were 55% for 5 steps and 43% for 8 steps from commercially available and inexpensive citraconic anhydride, respectively.
Straightforward Access to a Great Diversity of Complex Biorelevant γ-Lactams Thanks to a Tunable Cascade Multicomponent Process
Mardjan, Muhammad Idham Darussalam,Mayooufi, Atef,Parrain, Jean-Luc,Thibonnet, Jér?me,Commeiras, Laurent
supporting information, p. 606 - 614 (2020/03/04)
This reviews surveys the preparation of a great diversity of complex biorelevant γ-lactam backbones thanks to scalable copper(I)-catalyzed cascade multicomponent processes.
Copper(I)-Catalysed Multicomponent Reaction: Straightforward Access to 5-Hydroxy-1H-pyrrol-2(5H)-ones
Mardjan, Muhammad Idham Darussalam,Parrain, Jean-Luc,Commeiras, Laurent
, p. 543 - 548 (2016/02/27)
A copper-catalysed multicomponent coupling reaction between readily available (Z)-3-iodoacrylic acids, terminal alkynes, and primary amines was developed to smoothly access a small library of 5-hydroxy-1H-pyrrol-2(5H)-ones in good yields. This practical and general process was applied to a short-steps synthesis of the natural product pulchellalactam.
Short synthesis of pulchellalactam
Hermet, Jean-Paul,Caubert, Virginie,Langlois, Nicole
, p. 2253 - 2257 (2007/10/03)
tert -Butyl 4-methyl-2-oxo-2,5-dihydro-1 H -pyrrole-1-carboxylate 4 was synthesized by a short two-step procedure: regioselective 1,3-dipolar diazomethane cycloaddition to N -Boc-pyrrolinone 2 and thermolysis of the adduct. The compound 4 could be converted in one step into pulchellalactam. Copyright Taylor & Francis Group, LLC.
Metal-catalysed radical cyclisations leading to N-heterocycles: New approaches to gabapentin and pulchellalactam
Bryans, Justin S.,Chessum, Nicola E.A.,Huther, Nathalie,Parsons, Andrew F.,Ghelfi, Franco
, p. 6221 - 6231 (2007/10/03)
The copper(I) or ruthenium(II)-mediated radical cyclisation of halo-amides has been utilised to afford functionalised pyrrolidinones via 5-endo-trig or 5-exo-trig radical cyclisation pathways. This methodology has been applied to novel and concise syntheses of the anti-epileptic drug gabapentin and the biologically active natural product pulchellalactam.
Efficient total synthesis of pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor
Li, Wen-Ren,Lin, Sung Tsai,Hsu, Nai-Mu,Chern, Meei-Shiou
, p. 4702 - 4706 (2007/10/03)
A new approach to a CD45 protein tyrosine phosphatase inhibitor, pulchellalactam, is described. The key step of the sequence involves addition and elimination of an enolic lactam in a single step and 70% yield, employing an organocuprate reagent. The resulting α,β-unsaturated lactam could be condensed with isobutyraldehyde to produce Z-pulchellalactam or converted into siloxypyrrole, which was subjected to the BF3·Et2O-promoted coupling reaction with isobutyraldehyde to afford E-pulchellalactam after E1-cB elimination and TFA deprotection. This first total synthesis afforded Z-pulchellalactam in six steps and 32% overall yield from Boc-glycine. The same sequence of reactions could also be applied to the liquid- or solid-phase synthesis of trifunctionalized pulchellalactam derivatives.
