72203-94-2

Upstream product

• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 
• 123-38-6 propionaldehyde 

Downstream Products

• 90128-95-3 (-)-(2S,2'R)-2-(methoxymethyl)-1-<(2'-methyl-3'-phenyl)propylideneamino>pyrrolidine 
• 72171-04-1 (-)-(2S,2'S)-2-(methoxymethyl)-1-<(2'-methyl-3'-phenyl)propylideneamino>pyrrolidine 
• 389837-67-6 (S)-2-methyl-5-oxohexanal 
• 825601-05-6 (2R,2S)-(-)-[3-benzyloxy-2-methylpropylidene][2-(methoxymethyl)pyrrolidin-1-yl]amine 
• 825601-16-9 (1R,1'R,2S)-(-)-[1-(2'-benzyloxy-1'-methylethyl)pentyl][2-(methoxymethyl)pyrrolidin-1-yl]amine 
• 146968-02-7 <5(2E,4S,6S),7S>-2,7-Anhydro-8,9,10,12,13-pentadeoxy-10-methylene-3,4-bis-C-<(phenylmethoxy)carbonyl>-12-(phenylmethyl)-5-(4,6-dimethyl-2-octenoate)-L-erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid phenylmethyl ester 
• 117555-29-0 (S)-2-Methyl-1-octanol tosylate 
• 7786-29-0 (S)-α-methyloctanal 
• 217460-28-1 (S)-(+)-2-methylpentyl p-nitrophenylsulfonate 
• 105-30-6 (R)-2-methylpentan-1-ol 
• 105-30-6 (S)-2-methyl-1-pentanol 
• 326591-12-2 (R)-(-)-2-methylpentyl p-nitrophenylsulfonate 

Relevant academic research and scientific papers

COMPOUNDS FOR INHIBITING WIP1, PRODRUGS AND COMPOSITIONS THEREOF, AND RELATED METHODS

The invention provides compounds useful in inhibiting the activity of a Wip1 protein in a cell as well as prodrugs thereof, related methods of use and compositions which include the aforesaid compounds and prodrugs thereof. The compounds comprise a ring structure having at least five functional groups bonded thereto, wherein each functional group is bonded to a different ring atom, and wherein the at least five functional groups comprise: (a) first (R1) and second (R3) moieties each comprising a phosphate group wherein these first and second moieties are separated by at least one ring atom; (b) first (R2) and second (R4) hydrophobic groups, wherein the first and second hydrophobic groups are separated by at least one ring atom, and wherein the first hydrophobic group is bonded to a ring atom located between the ring atoms to which the first (R1) and second (R2) moieties are bonded; and an amide or carboxylic acid (R5).

Asymmetric synthesis of 6-alkyl- And 6-arylpiperidin-2-ones. Enantioselective synthesis of (S)-(+)-coniine

A variety of diolefinic hydrazides (1) have been assembled in a highly diastereoselective manner by addition of allyllithium to chiral SAMP hydrazones followed by N-acylation with acryloyl chloride. Substrates 1 undergo ring-closing metathesis to give the cyclic enehydrazides (5) which can be easily converted into virtually enantlopure 6-alkyl- or 6-arylpiperidin-2-ones (7). The versatility of this hydrazone addition-RCM protocol has been further exemplified by the conversion of the unsaturated heterocycle 5b into the piperidine alkaloid (S)-(+)-coniine.

Asymmetric synthesis of β-substituted γ-lactams employing the samp-/ramp-hydrazone methodology. Application to the synthesis of (R-(-)-baclofen

A short and efficient asymmetric synthesis of β-substituted γ-lactams is described. Key steps are the α-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The β-substituted γ-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee=93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (γ-aminobutyric acids) is demonstrated for (R-(-)-baclofen hydrochloride, which is obtained in 4 steps 55% yield and 94% ee.

First asymmetric synthesis of both enantiomers of Tropional and their olfactory evaluation

The first asymmetric synthesis of both enantiomers of Tropional is accomplished by asymmetric alkylation by employing the SAMP/RAMP-hydrazone method, respectively. The alkylated hydrazones were oxidatively cleaved with magnesium-monoperoxyphthalate (MMPP). Subsequent reduction of the resulting nitriles with diisobutyl aluminium hydride (DIBAL-H) led to the desired aldehydes in good overall yields (52-53%) and enantiomeric excesses (ee=90%). Furthermore, the olfactory evaluation of both enantiomers showed remarkable differences in odour quality and intensity.

Asymmetric synthesis of all stereoisomers of 7,11-dimethylheptadecane and 7-methylheptadecane, the female pheromone components of the spring hemlock looper and the pitch pine looper

The asymmetric synthesis of the stereoisomers of 7,11-dimethylheptadecane (1) and 7-methylheptadecane (2) via α-alkylation employing the SAMP/RAMP hydrazone method with high asymmetric induction and good overall yields is described. A mixture of (7S,11R)-1 and (S)-2 is the female-produced sex pheromone of the spring hemlock looper moth (Lambdina athasaria) and the pitch pine looper moth (Lambdina pellucidaria). They are both forest pests in northeastern North America.

Reaction of the lithio-derivative of methoxyallene with hydrazones. Part 1: Synthesis and transformation of α-allenyl hydrazines

The lithio-derivative of methoxyallene reacts with aldehyde hydrazones leading to expected α-allenyl hydrazines when ether is the solvent of the reaction. The yields are good as well as the diastereoselectivity observed in the case of SAMP-hydrazones. These hydrazines are cleanly transformed to N-dialkylamino-3-methoxy-3-pyrrolines when they are reacted with n-BuLi in THF. These compounds are sometimes accompanied by the isomeric 4-methyl azetidines. The N-dialkylamino-3-methoxy-3-pyrrolines are transformed to 3-methoxy-3-pyrrolines by hydrogenolysis of the nitrogen-nitrogen bond, to 3-alkoxy-pyrroles by treatment with a peracid and to 3-amino-pyrroles by acidic migration of the dialkylamino group. In the case of SAMP-hydrazines, the obtained 3-methoxy-3-pyrrolines have a high enantiomeric purity. Lastly, attempts to prepare α-hydrazino-esters (and subsequently α-amino-esters) by ozonolysis of the allenyl moiety failed due to the formation of a methyl glyoxylate.

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.

First asymmetric synthesis of 6-methyl-3-nonanone, the female-produced sex pheromone of the caddisfly Hesperophylax occidentalis

The asymmetric synthesis of the female-produced sex pheromone of the caddisfly Hesperophylax occidentalis, (S)-and (R)-6-methyl-3-nonanone, starting from the simple starting materials propanal, propyl iodide and 2-butanone, in good overall yields is described. The stereogenic centre at the C-6 position of the pheromone was generated via α-alkylation employing the SAMP/RAMP hydrazone method with high asymmetric induction (ee = 94 and 92%).

Stereoselective total synthesis of reveromycin B and C19-epi-reveromycin B

Our studies toward the total synthesis of the reveromycin family of natural products are described herein. Our synthetic approach is efficient, stereocontrolled, and convergent and has resulted in the first synthesis of reveromycin B (4) and C19-epi-reveromycin B (55). Key steps of this successful strategy include: a modified Negishi coupling (construction of C7-C8 bond) and a Kishi-Nozaki reaction (construction of C19-C20 bond), which were employed in the attachment of the target side chains. The key building blocks for the total synthesis were thus defined as vinyl iodide 6, alkyne 7, and alkyne 8. Our synthesis illustrates the utility of the modified Negishi coupling for the construction of complex dienes, confirms the proposed stereochemistry of reveromycins and paves the way for the preparation of designed analogues for biological study.

A short asymmetric synthesis of (-)-neonepetalactone

(4S.,4aR)-Neonepetalactone (6) was synthesized in high diastereomeric and enantiomeric purity (de, ee ≥ 96 %) in a four step procedure. Key step of the total synthesis is the Michael addition of metalated propanal SAMP-hydrazone ((S)-1) to 2-cyclopentenecarboxylate (2).