126410-45-5

Upstream product

• 100-39-0 benzyl bromide 
• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 3978-80-1 Boc-Tyr-OH 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 100-44-7 benzyl chloride 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 27513-44-6 N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester 
• 1026977-99-0 C₂₆H₃₃NO₇ 

Downstream Products

• 313679-49-1 C₂₃H₂₇NO₄ 
• 813460-81-0 (?)-spiroleucettadine 
• 228868-08-4 [3-(4-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propylamino]-acetic acid methyl ester 
• 1265146-01-7 C₂₈H₃₃NO₃ 
• 1265146-00-6 C₃₃H₄₄N₂O₅ 
• 1265145-90-1 C₃₃H₄₆N₂O₆ 
• 244228-08-8 C₃₃H₃₈N₂O₆ 
• 244228-07-7 C₃₅H₄₄N₄O₅ 
• 244228-06-6 C₃₆H₄₄N₄O₅ 
• 244228-05-5 C₂₈H₃₅N₃O₆ 

Relevant academic research and scientific papers

Strategies, Setbacks, and Successes in the Synthesis of (-)-Spiroleucettadine

Various strategies toward the synthesis of the marine natural product (-)-spiroleucettadine are described. In the original strategy, a biomimetic inspired oxidation of a 2-imidazoline scaffold uncovered unexpected reactivity, where benzylic oxidation followed by a Baeyer-Villiger reaction was observed. The second generation approach examined oxidative dearomatization of the phenol ring system first, where a competing spirocyclization process was uncovered. Efforts to forge the scaffold via a carbocation mediated benzyl migration were unsuccessful. Highlights of the successful synthesis include two consecutive hypervalent iodine reactions: the first formed the spirocyclic center and the second facilitated installation of an acetate group at the C-5 position to allow for subsequent introduction of the methyl amine side chain.

One-pot synthesis of Weinreb amides employing 3,3-dichloro-1,2-diphenylcyclopropene (CPI-Cl) as a chlorinating agent

The synthesis of Nα-protected amino alkyl Weinreb amides starting from the corresponding α-amino acids as well as carboxylic acids has been delineated through the in situ generation of acid chlorides using CPI-Cl as a chlorinating agent. The protocol is simple; the reaction conditions employed were mild, and compatible with all the three commonly used urethane protecting groups namely, Boc, Cbz and Fmoc groups. The resulting Weinreb amides are obtained in good yields as optically pure products.

Total Synthesis of (?)-Spiroleucettadine

One of a number of intriguing new alkaloids isolated from the Leucetta sp. sponge in 2004, spiroleucettadine displayed unique structural features on a restricted scaffold: a trans-fused 5,5-bicyclic ring system together with an amino hemiketal moiety. Attempts to synthesize the initially proposed structure failed, raising questions as to its veracity, and structure revision ensued in 2008; no successful synthetic approach has been reported to date. Herein, we describe the enantiospecific total synthesis of (?)-spiroleucettadine by a highly efficient biomimetic approach starting from l-tyrosine. One of two key hypervalent-iodine-mediated oxidation reactions forged the spirocyclic center, and the other enabled the installation of the methylamine side chain in the penultimate step. Our approach provides synthetic access to a new class of spiroannulated natural products and will enable future studies of the structure–biological-activity relationships of these antibacterial compounds.

Structure and absolute configuration of auriculamide, a natural product from the predatory bacterium herpetosiphon aurantiacus

The genome of the filamentous, predatory bacterium Herpetosiphon aurantiacus harbors a plethora of genes that are predicted to be involved in natural product biosynthesis. Until now, however, no secondary metabolites have been described from this microorganism. Analysis of H. aurantiacus culture extracts by 1H NMR spectroscopy now led to the discovery of a chlorinated amide, which we termed auriculamide. The configuration of the three chiral centers in auriculamide was solved by chromatographic comparison with stereospecifically prepared reference compounds following chemical degradation. Furthermore, a putative gene cluster for the biosynthesis of auriculamide was identified by genome mining. Chemical analysis of culture extracts from the predatory bacterium Herpetosiphon aurantiacus led to the discovery of the new natural product auriculamide, the structure of which was elucidated by MS and NMR analyses. The absolute configuration was determined, after hydrolysis, by chromatographic comparison with synthetic standards. A gene cluster for the biosynthesis of auriculamide is proposed.

Pyrrole-based scaffolds for turn mimics

Two amino acid derived synthons were combined to give homopropargylic amines 2. Platinum dichloride was used to cyclize these intermediates into pyrroles 3 which collapsed to the target secondary structure mimics 1 on treatment with base. Side chains of these compounds overlay with an idealized type 1 β-turn and with an inverse γ-turn.(Figure Presented)

PEPTIDE TURN MIMETICS

Peptide mimetics of structure X herein which (i) provide a wide range of sidechain functions at all sidechain positions, (ii) can be incorporated in a peptide sequence, (iii) can be readily synthesized and (iv) have a variety of conformations. There is also provided a novel process which can provide valuable intermediates in relation to production of peptide mimetics of structure X which intermediates have a high degree of chemo- and stereo-selectivity. Preferred mimetics include structures I, II, III, IV, V and VI.

Inhibitors of aspartyl protease

The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.

Synthesis of new chiral peptide nucleic acid (PNA) monomers by a simplified reductive amination method

The aim of this work was the preparation of four new peptide nucleic acid (PNA) monomer backbone by reductive amination of N(α)-Boc-protected chiral amino aldehydes, derived from Leu, Phe, Tyr(Bzl), and Thr(Bzl), with methyl glycinate. To the crude 2-subs

Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1'phenyl substituents: X-ray crystal structure assisted design

By tethering of a polar hydrophilic group to the P1 or P1' substituent of a Phe-based hydroxyethylene isostere, the antiviral potency of a series of HIV protease inhibitors was improved. The optimum enhancement of anti-HIV activity was observed with the 4-morpholinylethoxy substituent. The substituent effect is consistent with a model derived from inhibitor docked in the crystal structure of the native enzyme. An X-ray crystal structure of the inhibited enzyme determined to 2.25 A verifies the modeling predictions.