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Subtype-selective agonists of the neurotensin receptor NTS2 represent a promising option for the treatment of neuropathic pain, as NTS2 is involved in the mediation of mu-opioid-independent anti-nociceptive effects. Based on the crystal structure of the subtype NTS1 and previous structure-activity relationships (SARs) indicating a potential role for the sub-pocket around Tyr11 of NT(8-13) in subtype-specific ligand recognition, we have developed new NTS2-selective ligands. Starting from NT(8-13), we replaced the tyrosine unit by beta2-amino acids (type 1), by heterocyclic tyrosine bioisosteres (type 2) and peptoid analogues (type 3). We were able to evolve an asymmetric synthesis of a 5-substituted azaindolylalanine and its application as a bioisostere of tyrosine capable of enhancing NTS2 selectivity. The S-configured test compound 2a, [(S)-3-(pyrazolo[1,5-a]pyridine-5-yl)-propionyl11]NT(8-13), exhibits substantial NTS2 affinity (4.8 nm) and has a nearly 30-fold NTS2 selectivity over NTS1. The (R)-epimer 2b showed lower NTS2 affinity but more than 600-fold selectivity over NTS1. Tyrosine surrogates: Peptides 2a,b showed that the 5-substituted azaindolylalanine is an appropriate bioisostere of tyrosine capable of enhancing NTS2 selectivity. Compound 2a exhibits single-digit nanomolar affinity (4.8 nm) and a nearly 30-fold NTS2 selectivity over NTS1.

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(Chemical Equation Presented) A stereoselective halo-etherification of chiral enamides is described here. This work provides an approach to halogen containing cyclic ethers and reveals further mechanistic insights to the chemistry of chiral enamides.

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Chemistry involves the study of all things chemical – chemical processes, chemical compositions and chemical manipulation – in order to better understand the way in which materials are structured, how they change and how they react in certain situations. Application In Synthesis of (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

In view of the prominent role of the 1H-indol-3-yl side chain of tryptophan in peptides and proteins, it is important to have the appropriately protected homologs H-beta2-HTrp-OH and H-beta3-HTrp-OH (Fig.) available for incorporation in beta-peptides. The beta2-HTrp building block is especially important, because beta2-amino acid residues cause beta-peptide chains to fold to the unusual 12/10 helix or to a hairpin turn. The preparation of Fmoc- and Z-beta2-HTrp(Boc)-OH by Curtius degradation (Scheme 1) of a succinic acid derivative is described (Schemes 2 – 4). To this end, the (S)-4-isopropyl-3-[(N-Boc-indol-3-yl)propionyl]-1,3-oxazolidin-2-one enolate is alkylated with Br-CH2CO2Bn (Scheme 3). Subsequent hydrogenolysis, Curtius degradation, and removal of the Evans auxiliary group gives the desired derivatives of (R)-H-beta2-HTrp-OH (Scheme 4). Since the (R)-form of the auxiliary is also available, access to (S)-beta2-HTrp-containing beta-peptides is provided as well.

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Fmoc-beta2hSer(tBu)-OH was converted to Fmoc-beta2hSec(PMB)-OH in five steps. To avoid elimination of HSeR, the selenyl group was introduced in the second last step (Fmoc- beta2hSer(Ts)-OAll?Fmoc-beta2hSec(PMB)-OAll). In a similar way, the N-Boc-protected compound was prepared. With the beta2hSe-derivatives, 21 beta2-amino-acid building blocks with proteinogenic side chains are now available for peptide synthesis. Copyright

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A mild method is presented for the formation of N-acylated oxazolidinones that employs acid fluorides and mild bases, such as iPr 2NEt and NEt3. Optimized reaction conditions for two types of substrates have been developed utilizing either the oxazolidinone itself or the corresponding in situ generated O-silyloxazolidinones resulting in the formation of the desired N-acylated products in high yields of up to 98%.

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The 4-isopropyl-5,5-diphenyloxazolidinone (1) is readily prepared from (R)- or (S)-valine ester, PhMgBr, and ethyl chlorocarbonate. It has a melting point of ca. 250, a low solubility in most organic solvents, and a C=O group which is sterically protected from nucleophilic attack. Thus, the soluble N-acyl-oxazolidinones (7-16) can be prepared from 1 with BuLi at temperatures around 0instead of – 78(Scheme 3), their Li enolates can be generated with BuLi, rather than with LDA, and deacylation in the final step of the procedure can be achieved with NaOH at ambient temperatures (Scheme 12), with facile recovery of the precipitating auxiliary 1 (filtering, washing, and drying). The following reactions of N-acyl-oxazolidinones from 1 have been investigated: alkylations (Scheme 4), aminomethylations and hydroxymethylations (Scheme 5), aldol additions (Schemes 6 and 7), Michael additions (Schemes 9 and 10), and a (4 + 2) cycloaddition (Scheme 11). The well-known features of reactions following the Evans methodology (yield, diastereoselectivity, dependence on conditions, counter ions, additives etc.) prevail in these transformations. Most products, however, have higher melting points and a much more pronounced crystallization tendency than those derived from conventional oxazolidinones, and can thus be purified by recrystallization, avoiding chromatography (Table 1). The disadvantage of 1 having a higher molecular weight (ca. 150 Da) than the non-phenyl-substituted auxiliary is more than compensated by the ease of its application, especially on large scale. A number of crystal structures of oxazolidinones derived from 1 and a TiCl4 complex of an oxazolidinone are described and discussed in view of the diastereoselective-reaction mechanisms.

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(Equation Presented) The 3-methylthiomethyl-4-isopropyl-5,5-diphenyl-1,3-oxazolidin-2-one (I, prepared in three steps from Boc-valine ester) is lithiated and added to aldehydes, with protecting in situ trapping of the primary adducts, to give the N,S-acetal derivatives II of 2-hydroxy a dehydes in high yields and diastereoselectivities. Cleavage (with ready recovery of the oxazolidinone auxiliary) is possible, to afford, for instance, enantiopure 1,2-diols, selectively protected (OBn, OMOM, OTBS) in the 2-position.

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The asymmetric desymmetrization of 3-substituted glutaric anhydrides 1 bearing silyl, aryl and alkyl groups with the lithium salt of chiral oxazolidin-2-ones has been studied. The effects of the substituents at the 4- and 5-positions of the oxazolidin-2-ones on the diastereoselectivity of the anhydride opening were studied in detail. A SuperQuat chiral oxazolidin-2-one 2e with 5,5-diaryl substituents showed optimum selectivity.

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We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2?CSP 4).

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A range of chiral ester and chiral imide derivatives of 2-oxocyclohexanecarboxylic acid were utilised in double-Mannich reactions with bis(aminol)ethers to develop an asymmetric synthesis of azabicyclo[3.3.1]nonanes. An improved method for the double-Mannich reaction of beta-ketoesters and bis(aminol)ethers using sub-stoichiometric quantities of a Lewis acid was developed. Additionally, a sequential, double-Mannich approach was investigated incorporating chiral auxiliaries into N,O-acetals. The use of oxazolidinone auxiliaries afforded the best yields and diastereoselectivities enabling separation of the resulting diastereomers of the azabicyclo[3.3.1]nonanes.

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