884-68-4

Basic information

• Product Name: Allosecurinin
• Synonyms: Allosecurinin;(2S)-Securinan-11-one;(2α)-Securinan-11-one;2-Allosecurinine;Phyllochrysine;Nsc107415;Securinan-11-one, (2.alpha.)-
• CAS NO: 884-68-4
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.2637
• Mol File: 884-68-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 136-138 °C
• Boiling Point: 459.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.30±0.1 g/cm3(Predicted)
• PKA: 8.29±0.20(Predicted)
• CAS DataBase Reference: Allosecurinin(CAS DataBase Reference)
• NIST Chemistry Reference: Allosecurinin(884-68-4)
• EPA Substance Registry System: Allosecurinin(884-68-4)

Safety Data

• Hazardous Substances Data: 884-68-4(Hazardous Substances Data)

Usage

General Description

Allosecurinin is a chemical compound that belongs to the class of secorapamycins, which are known for their antibacterial properties. It is produced by the bacterium Saccharomonospora, and studies have shown that allosecurinin has potent activity against a wide range of Gram-positive bacteria, including drug-resistant strains. This makes it a promising candidate for the development of new antibiotics to combat antibiotic-resistant infections. Allosecurinin has also been found to have low toxicity to human cells, further demonstrating its potential for use as a therapeutic agent. Overall, allosecurinin shows promise as a natural product with significant potential for addressing the growing problem of antibiotic resistance.

Upstream product

• 30155-11-4 (2α)-14ξ-hydroxy-14,15-dihydro-securinan-11-one 
• 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 
• 651737-98-3 1(S)-[(2'R)-N-tert-butoxycarbonylpiperidinyl]-1-ethynyl-4(Z)-hepten-1-ol 
• 651738-03-3 1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-9-oxabicyclo[4.3.0]nona-4,6-diene 
• 651737-95-0 1-tert-butoxycarbonyl-2(R)-[4'(Z)-heptenoyl]piperidine 
• 708260-76-8 tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate 
• 651738-04-4 tert-butyl (2R)-2-[(7aS)-2(6H)-oxo-7,7a-dihydro-7a-benzofuranyl]piperidine-1-carboxylate 
• 651738-07-7 1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene 
• 14140-69-3 (RS)-1-formyl-2-((7aSR)-6ξ-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7ar-yl)-piperidine 
• 1126784-62-0 (2S,4R)-1-tert-butyl 2-methyl 5-acetoxy-4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate 

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 
• 1085244-08-1 (2β,15α)-14,15-dihydro-15-[4-(4-methoxyphenyl)piperazin-1-yl]securinan-11-one 
• 1085244-06-9 (2β,15α)-14,15-dihydro-15-(4-phenylpiperazin-1-yl)securinan-11-one 
• 3909-79-3 Tetrahydrosecurinin 

Relevant articles and documents

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.

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

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.