1857-30-3

Upstream product

• 119817-92-4 securinol A 
• 15848-22-3 5-bromo-1-pentanyl acetate 
• 34626-51-2 5-bromopentan-1-ol 
• 170220-11-8 5-azido-1-pentanol 
• 114642-97-6 5-azido-1-pentanal 
• 111-29-5 1 ,5-pentanediol 
• 119817-92-4 Securinol B 
• 735315-17-0 (R)-2-((Z)-(R)-1-Allyloxy-1-trimethylsilanylethynyl-hept-4-enyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 735315-16-9 (R)-2-((Z)-(R)-1-Hydroxy-1-trimethylsilanylethynyl-hept-4-enyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 735315-18-1 (R)-2-((Z)-(R)-1-Allyloxy-1-ethynyl-hept-4-enyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 735315-21-6 2-(2-oxo-6,7-dihydro-2H-benzofuran-7a-yl)-piperidine-1-carboxylic acid tert-butyl ester 
• 735315-19-2 2-(6,7-dihydro-2H-benzofuran-7a-yl)-piperidine-1-carboxylic acid tert-butyl ester 
• 651737-95-0 1-tert-butoxycarbonyl-2(R)-[4'(Z)-heptenoyl]piperidine 
• 735315-23-8 2-(6-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7a-yl)-piperidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 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

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.

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.

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.

First total synthesis of (+)-viroallosecurinine

The first diastereoselective chiral synthesis of (+)-viroallosecurinine, isolated from Securinega virosa as a cytotoxic alkaloid, was achieved by using a chelation-controlled addition of an alkyne moiety to the corresponding ketone, and a ring-closing metathesis, as key reactions.

Bio-inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)-Virosine B and (?)-Episecurinol A

The so-called Securinega alkaloids constitute a class of tetracyclic biologically active specialised metabolites isolated principally from subtropical plants belonging to the Phyllanthaceae family. Following a strategy based on alternative hypotheses for their biosynthesis, an easy and time-efficient divergent synthesis enabled access to twelve of those alkaloids featuring (neo)(nor)securinane skeletons. Moreover, this work permitted to reassign the absolute configurations of (+)-virosine B and (?)-episecurinol A.

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.

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.