884-68-4

Usage

Uses

Used in Pharmaceutical Industry:
Allosecurinin is used as an antibiotic for its potent activity against a wide range of Gram-positive bacteria, including drug-resistant strains. Its low toxicity to human cells makes it a promising candidate for the development of new therapeutic agents to address the growing problem of antibiotic resistance.
Used in Research and Development:
Allosecurinin is utilized in the research and development of new antibiotics, as it demonstrates significant potential in combating antibiotic-resistant infections. Its unique properties and low toxicity to human cells make it an attractive option for further exploration and development in the field of antimicrobial agents.

Upstream product

• 30155-11-4 (2α)-14ξ-hydroxy-14,15-dihydro-securinan-11-one 
• 267420-70-2 1-(tert-butyl) 2-methyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate 
• 941576-02-9 methyl-1-tert-butyl-(2S,4R)-4{[tert-butyl(dimethyl)silyl]-oxy}-5-hydroxy-pyrrolidine-1,2-dicarboxylate 
• 201230-82-2 carbon monoxide 
• 1126784-62-0 (2S,4R)-1-tert-butyl 2-methyl 5-acetoxy-4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate 
• 14140-69-3 (RS)-1-formyl-2-((7aSR)-6ξ-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7ar-yl)-piperidine 
• 1126784-60-8 (1'S,3'S,8a'R)-3'-((Z)-2-iodovinyl)-3',5',6',7',8',8a'-hexahydro-2'H,5H-spiro[furan-2,1'-indolizin]-5-one 
• 5890-59-5 (RS)-7a-(SR)-piperidin-2-yl-7,7a-dihydro-6H-benzofuran-2-one 
• 14140-68-2 (RS)-1-formyl-2-((SR)-2-oxo-6,7-dihydro-2H-benzofuran-7a-yl)-piperidine 
• 651737-96-1 1(S)-[(2''R)-N-tert-butoxycarbonylpiperidinyl]-1-(2'-trimethylsilylethynyl)-4(Z)-hepten-1-ol 
• 651737-99-4 1-tert-butoxycarbonyl-2(R)-[1'(S)-allyloxy-1'-ethynyl-4'(Z)-heptenyl]piperidine 

Downstream Products

• 42496-75-3 1α-amino-11-oxo-(2α)-securinanium; 2,4,6-trimethyl-benzenesulfonate 
• 42555-40-8 1β-amino-11-oxo-securinanium; 2,4,6-trimethyl-benzenesulfonate 
• 3909-79-3 Tetrahydrosecurinin 
• 1085244-06-9 (2β,15α)-14,15-dihydro-15-(4-phenylpiperazin-1-yl)securinan-11-one 
• 1085244-08-1 (2β,15α)-14,15-dihydro-15-[4-(4-methoxyphenyl)piperazin-1-yl]securinan-11-one 

Relevant academic research and scientific papers

Tungsten-Promoted Hetero-Pauson-Khand Cycloaddition: Application to the Total Synthesis of (-)-Allosecurinine

Herein, we report a concise enantioselective synthesis of (-)-allosecurinine, a tetracyclic Securinega alkaloid featuring an α,β-unsaturated γ-lactone moiety. Starting from inexpensive and readily available trans - l -hydroxyproline, our strategy entails a rare late-stage [2+2+1]-hetero-Pauson-Khand cycloaddition between a ketone and an alkyne as the key complexity-generating step to rapidly install the CD-ring system. The reported W(CO) 6 -promoted intramolecular cyclization provides the first example of a tungsten-mediated hetero-Pauson-Khand reaction. This approach to the strained bicyclic CD motif present in allosecurinine provides some insights into the boundaries of this potentially powerful methodology that might be further extended to other butenolide-containing natural products.

Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu'amamine E/ent-Virosine A and Bubbialine

The synthesis of the Securinega alkaloid secu'amamine E (ent-virosine A) has been accomplished for the first time in 12 steps and 8.5% overall yield. In addition, bubbialine has been prepared and characterized. These two alkaloids and bubbialidine, all featuring an azabicyclo[2.2.2]octane core, were rearranged to their azabicyclo[3.2.1]octane congeners, a framework found in many Securinega alkaloids. These experiments suggest that azabicyclo[2.2.2]octane derivatives could serve as intermediates in the biosynthesis of the rearranged azabicyclo[3.2.1]octane products.

Enantioselective approach to securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine

(Chemical Equation Presented) The most representative securinega alkaloids have been synthesized through a new strategy involving the palladium-catalyzed enantioselective allylation of a cyclic imide, a vinylogous Mannich reaction, and a ring-closing meta

The asymmetric total synthesis of (-)-securinine

The alkaloid (-)-securinine was synthesized in 18 steps and 16% overall yield from trans-4-hydroxy-l-proline. The Royal Society of Chemistry.

Total synthesis of (-)-allosecurinine

(Chemical Equation Presented) Safe and secure: An efficient methodology which provides access to homochiral 2,5-cis pyrrolidines in excellent yields starting from chiral alkoxyamine cyclopropanes was used in the total synthesis of (-)-allosecurinine (see

Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide

(Chemical Equation Presented) A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide.

First Diastereoselective Chiral Synthesis of (-)-Securinine

(Equation presented) A diastereoselective total synthesis of securinine in optically pure form was achieved by employing ring-closing metathesis of the corresponding dienyne compound as a key step.

A new general access to either type of securinega alkaloids: Synthesis of securinine and (-)-allonorsecurinine

Matrix presented. The syntheses of securinine and (-)-allonorsecurinine have been achieved starting from easily available α-amino acid derivatives and using as key steps a RCM and a Heck reaction for the formation of rings D and C, respectively.

Kinetics and mechanism of the alkaline hydrolysis of securinine

The hydroxide ion-catalyzed hydrolysis of securinine involves the ring opening of the lactone moiety. The rate of hydrolysis is insensitive to the ionic strength. The observed pseudo-first-order rate constants reveal a decrease of approximately 4-fold due to the increase in the MeCN content from 4 to 50% (v/v) in mixed aqueous solvent. The temperature dependence of the rate of hydrolysis follows the Eyring equation, which yields ΔH* and ΔS* as 11.0 kcal mol-1 and -34.5 cal deg-1 mol-1, respectively. The hydroxy carboxylate product of the alkaline hydrolysis of securinine is shown to undergo cyclization in acidic medium to yield securinine. The observed pseudo-first-order rate constants for cyclization increase linearly with an increase in [H+]. The change in the content of MeCN from 3.8 to 47.2% (v/v) in mixed aqueous solvents does not show an effect on the rate of the cyclization reaction. The most plausible mechanisms for alkaline hydrolysis and acid cyclization reactions are also discussed.