2650-35-3Relevant academic research and scientific papers
Stereoselective total syntheses of (-)-flueggine A and (+)-virosaine B
Wei, Hao,Qiao, Chuang,Liu, Gang,Yang, Zhen,Li, Chuang-Chuang
, p. 620 - 624 (2013)
Convergent approach: The total syntheses of (-)-flueggine A and (+)-virosaine B (see scheme) have been accomplished in a concise and convergent manner. Key steps in these approaches were relay ring-closing metathesis reactions for rapid construction of the key intermediates, and 1,3-dipolar cycloaddition reactions for the formation of the natural products. Copyright
Bio-inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)-Virosine B and (?)-Episecurinol A
Antien, Kevin,Cossío, Fernando P.,Deffieux, Denis,Lacambra, Aitor,Massip, Stéphane,Peixoto, Philippe A.,Pouységu, Laurent,Quideau, Stéphane
supporting information, (2019/08/21)
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
Gonzalez-Galvez, David,Garcia-Garcia, Elena,Alibes, Ramon,Bayon, Pau,De March, Pedro,Figueredo, Marta,Font, Josep
scheme or table, p. 6199 - 6211 (2010/01/06)
(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
An effective enantioselective approach to the securinega alkaloids: Total synthesis of (-)-norsecurinine
Alibes, Ramon,Bayon, Pau,De March, Pedro,Figueredo, Marta,Font, Josep,Garcia-Garcia, Elena,Gonzalez-Galvez, David
, p. 5107 - 5109 (2007/10/03)
(Chemical Equation Presented) A highly versatile approach to the enantioselective synthesis of securinega alkaloids is presented. Crucial steps are a palladium-catalyzed enantioselective imide alkylation, a vinylogous Mannich reaction, and a ring-closing
Total syntheses of the Securinega alkaloids (+)-14,15-dihydronorsecurinine, (-)-norsecurinine, and phyllanthine
Han, Gyoonhee,LaPorte, Matthew G.,Folmer, James J.,Werner, Kim M.,Weinreb, Steven M.
, p. 6293 - 6306 (2007/10/03)
A new strategy for enantiospecific construction of the Securinega alkaloids has been developed and applied in total syntheses of (+)-14,15-dihydronorsecurinine (8), (-)-norsecurinine (6), and phyllanthine (2). The B-ring and C7 absolute stereochemistry of these biologically active alkaloids originated from trans-4-hydroxy-L-proline (10), which was converted to ketonitrile 13 via a high-yielding eight-step sequence. Treatment of this ketonitrile with SmI2 afforded the 6-azabicyclo-[3.2.1]octane B/C-ring system 14, which is a key advanced intermediate for all three synthetic targets. Annulation of the A-ring of (-)-norsecurinine (6) with the required C2 configuration via an N-acyliminium ion alkylation was accomplished using radical-based amide oxidation methodology developed in these laboratories as a key step, providing tricycle 33. Annulation of the D-ring onto α-hydroxyketone 33 with the Bestmann ylide 45 at 12 kbar gave (+)-14,15-dihydronorsecurinine (8). In the securinine series, the D-ring was incorporated using an intramolecular Wadsworth-Horner-Emmons olefination of phenylselenylated α-hydroxyketone 47. The C14,15 unsaturation was installed late in the synthesis by an oxidative elimination of the selenoxide derived from tetracyclic butenolide 50 to give (-)-norsecurinine (6). The A-ring of phyllanthine (2) was formed from hydroxyketone 14 using a stereoselective Yb(OTf)3-promoted hetero Diels-Alder reaction of the derived imine 34 with Danishefsky's diene, affording adduct 35. Conjugate reduction and stereoselective equatorial ketone reduction of vinylogous amide 35 provided tricyclicintermediate 36, which could then be elaborated in a few steps to stable hydroxyenone 53 via α-selenophenylenone intermediate 52. The D-ring was then constructed, again using an intramolecular Wadsworth-Horner-Emmons olefination reaction to give phyllanthine (2).
Synthesis of the Securinega Alkaloids (+/-)-Norsecurinine and (+/-)-Nirurine from 3-Hydroxypyridine
Magnus, Philip,Rodriguez-Lopez, Julian,Mulholland, Keith,Matthews, Ian
, p. 8059 - 8072 (2007/10/02)
Treatment of the dihydropyridine 5 with fluoride anion resulted in in situ formation of the allenylidene 4 which cyclized to the azabicyclooctene 9.Subsequent elaboration to the alcohol 24 and rearrangement gave norsecurinine 2.The intermediate dio
Bis-heteroannulation. 15. Enantiospecific syntheses of (+)and (-)-norsecurinine
Jacobi, Peter A.,Blum, Charles A.,DeSimone, Robert W.,Udodong, Uko E. S.
, p. 5384 - 5392 (2007/10/02)
(-)-Norsecurinine (2a) has been prepared in a stereospecific fashion with the acetylenic oxazole 39 as the starting material. Diels-Alder cyclization of 39 afforded the furano ketone 45 that was transformed in five steps to the butenolide mesylate 52. Tra
TOTAL SYNTHESIS OF (+)- AND (-)-NORSECURININE
Jacobi, Peter A.,Blum, Charles A.,DeSimone, Robert W.,Udodong, Uko E. S.
, p. 7173 - 7176 (2007/10/02)
(-)-Norsecurinine (1a) has been prepared in a stereospecific fashion beginning with the acetylenic oxazole 18.Diels-Alder cyclization of 18 afforded the furanoketone 19, which was transformed in five steps to the butenolide mesylate 24.Transannular alkyla
