76831-46-4Relevant academic research and scientific papers
A divergent approach to the diastereoselective synthesis of several ant-associated Lridoids
Beckett, Joel S.,Beckett, James D.,Hofferberth, John E.
, p. 1408 - 1411 (2010)
(Figure Presented) The ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the individual antipodes of actinidine by a novel tandem cycloaddition/ pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial.
Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones
Zimmermann, Nicole,Hilgraf, Robert,Lehmann, Lutz,Ibarra, Daniel,Francke, Wittko
scheme or table, p. 1246 - 1255 (2012/10/08)
Starting from the enantiomers of limonene, all eight stereoisomers of trans-fused dihydronepetalactones were synthesized. Key compounds were pure stereoisomers of 1-acetoxymethyl-2-methyl-5-(2-hydroxy-1-methylethyl)-1- cyclopentene. The stereogenic center of limonene was retained at position 4a of the target compounds and used to stereoselectively control the introduction of the other chiral centers during the synthesis. Basically, this approach could also be used for the synthesis of enantiomerically pure trans-fused iridomyrmecins. Using synthetic reference samples, the combination of enantioselective gas chromatography and mass spectrometry revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain the enantiomerically pure trans-fused (4R,4aR,7R,7aS)-dihydronepetalactone as a minor component, showing an unusual (R)-configured stereogenic center at position 7.
Scope and applications of second generation palladium-catalyzed cycloalkenylation. Stereoselective total syntheses of isoiridomyrmecin, isodihydronepetalactone, and α-skytanthine
Takeda, Kazutaka,Toyota, Masahiro
, p. 9909 - 9921 (2012/02/06)
Functionalized bicyclo[3.2.1]octanes, -oxabicyclo-[4.3.0]nonanes, 3-azabicyclo[3.3.0]octanes, and 3-azabicyclo[4.3.0]nonanes were easily synthesized via a second generation palladium-catalyzed cycloalkenylation. Isoiridomyrmecin and isodihydronepetalactone, both of which feature a 3-oxabicyclo[4.3.0]nonane subunit, were stereoselectively synthesized via a second generation palladium-catalyzed cycloalkenylation as the key step. α-Skytanthine, a typical 3-azabicyclo[4.3.0]nonane alkaloid, was also constructed using the same catalytic cyclization protocol.
Efficient Oxidative Radical Cyclizations of Ester Enolates with Carbocation Desilylation as Termination: Synthesis of Cyclopentanoid Monoterpenes and Analogues
Jahn, Ullrich,Hartmann, Philip,Kaasalainen, Emmi
, p. 257 - 260 (2007/10/03)
(Matrix presented) An efficient oxidative radical cyclization approach for the synthesis of 2-alkenyl cyclopentane or cyclohexane carboxylates from ω-silylallyl ester enolates induced by recyclable SET oxidant ferrocenium hexafluorophosphate has been deve
Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of (±)-dihydronepetalactone using the SE2′ reaction of an allylsilane
Fleming, Ian,Terrett, Nicholas K.
, p. 2645 - 2649 (2007/10/03)
A propargylic alcohol 24 with the propynyl group exo on the norbornene framework was used in a stereospecific synthesis of the mixture of allylsilanes 27 and 28. The stereospecific reaction of this mixture with peracid gave, with a high level of stereocon
New Type of Cyclization of α,β,χ,ψ-Unsaturated Dioic Acid Esters through Tandem Conjugate Additions by Using Lithium N-Benzyl-N-(trimethylsilyl)amide as a Nitrogen Nucleophile
Uyehara, Tadao,Shida, Naomi,Yamamoto, Yoshinori
, p. 3139 - 3145 (2007/10/02)
Treatment of dimethyl (2E,6E)-2,6-octadienedioate with lithium N-benzyl-N-(trimethylsilyl)amide (LSA) gave 5-exo-trig ring closure products, methyl 3-(N-benzylamino)-2-(methoxycarbonyl)cyclopentane-1-acetates, through tandem conjugate additions.The relate
Cyclisation of α,β,χ,ψ-Unsaturated Dioic Acid Esters via Tandem Conjugate Additions by using Lithium N-Benzyltrimethylsilylamide (LSA) as a Nitrogen Nucleophile and its Application to a Total Synthesis of (+/-)-Dihydronepetalactone and (+/-)-Isodihydronep
Uyehara, Tadao,Shida, Naomi,Yamamoto, Yoshinori
, p. 113 - 114 (2007/10/02)
A stereoselective total synthesis of (+/-)-dihydronepetalactone and (+/-)-isodihydronepetalactone has been accomplished by utilising a novel cyclisation procedure; a reaction of octadiene-2,6-dioic acid esters with lithium N-benzyltrimethylsilylamide (LSA
CLAISEN-REARRANGEMENT-MEDIATED RING CONTRACTION OF MACROCYCLIC LACTONES A NEW APPROACH TO CARBOCYCLES AND HETEROCYCLES
Funk, Raymond L.,Abelman, Matthew, M.,Munger, John D.
, p. 2831 - 2846 (2007/10/02)
Macrocyclic ketene acetals 3 undergo Claisen rearrangements smoothly and constitute a viable and general approach to hetero- or carbocyclic ring systems 4.This novel ring contraction process is subject to high internal asymmetric induction (cf. lactones 7 -> carbocycles 8) as well as relative asymmetric induction in the rearrangements of ketene acetals derived from lactones 18, 23 and 27.Finally, N-benzoylmeroquinene methyl ester (37) was prepared to demonstrate the potential of this methodology in heterocycle synthesis.
STEREOSPECIFIC ALLYLSILANE REACTIONS: A TOTAL SYNTHESIS OF DIHYDRONEPETALACTONE
Fleming, Ian,Terrett, Nicholas K.
, p. 5103 - 5104 (2007/10/02)
A stereospecific synthesis of allylsilanes and their stereospecific reaction with peracid are used to prepare the endo-prop-1-enylnorbornenol (6), a substrate for an oxy-Cope rearrangement leading eventually to dihydronepetalactone (10) with complete stereocontroll.
