573-94-4

Usage

InChI:InChI=1/C10H16O2/c1-6-3-4-8-7(2)10(11)12-5-9(6)8/h6-9H,3-5H2,1-2H3/t6-,7+,8+,9+/m1/s1

Upstream product

• 107485-97-2 δ-iridodiol 
• 60419-55-8 (+)-teucriumlactone 
• 131726-13-1 (4aR,7S,7aR)-Hexahydro-7-methylcyclopenta[c]pyran-3-one 
• 74-88-4 methyl iodide 
• 261511-35-7 (2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid 
• 883997-14-6 ethyl (4S,5S)-5,6-isopropylidene-4-methylhexanoate 
• 883997-13-5 ethyl (4S,5S,2E)-5,6-isopropylidene-4-methylhexanoate 
• 883997-25-9 methyl (2E,6S,7S)-7,8-dihydroxy-2,6-dimethyl-2-octenoate 
• 883997-27-1 methyl (2E,6S,7S)-8-tert-butyldimethylsiloxy-7-hydroxy-2,6-dimethyl-2-octenoate 
• 883997-32-8 methyl (2E,6S,7S)-8-tert-butyldimethylsiloxy-2,6-dimethyl-7-[(phenoxythiocarbonyl)oxy]-2-octenoate 
• 74243-88-2 (βS,4S)-β,2,3-trimethyl-1,3-dioxolane-4-ethanol 
• 144938-82-9 (1S,4R)-(+)-4-(Hydroxymethyl)cyclopent-2-enol 
• 261511-33-5 (3S,3aS,4R,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-3-methylcyclopenta[b]furan-2-one 
• 261511-22-2 (1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol 

Downstream Products

• 485-43-8 isoiridomyrmecin 
• 485-43-8 iridomyrmecin 
• 485-43-8 (+/-)-Isoiridomyrmecin 

Relevant academic research and scientific papers

Preparation method of isoiridomyrmecin

The invention relates to a preparation method of isoiridomyrmecin, which comprises the following steps: (1) by using a compound 1: 4, 7-dimethyl-1, 4a, 5, 6, 7, 7a-hexahydrocyclopentapyran as a raw material, sequentially adding benzyl alcohol, trichloroacetonitrile and a silicon reagent into a solvent for a nucleophilic addition reaction to obtain a compound 2, (2) removing benzyl from the compound 2 and a palladium reagent in the solvent through hydrogen to prepare a compound 3, and (3) sequentially adding N-methyl morpholine oxide, tetrapropylammonium perruthenate and a molecular sieve intothe compound 3 in a solvent, and oxidizing to obtain the isoiridomyrmecin. Compared with the prior art, the method provided by the invention has the advantages of simple operation process, mild reaction conditions, relative environmental friendliness, no use of highly toxic products, high yield and the like, and can be used for large-scale production.

Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: An intramolecular Pauson-Khand reaction based one-stop synthetic solution

A simple and general approach towards the total syntheses of several iridolactones such as (±)-boschnialactone, (±)-7-epi-boschnialactone, (±)-teucriumlactone, (±)-iridomyrmecin, (±)-isoboonein, (±)-7-epi-argyol, (±)-scabrol A, (±)-7-epi-scabrol A, and (±)-patriscabrol as well as the putative structure of scholarein A is delineated. The synthetic strategy features a diastereoselective intramolecular Pauson-Khand reaction (IPKR) to construct the iridoid framework followed by some strategic synthetic manipulations to access the targeted monoterpenes including those having diverse oxy-functionalization patterns and with 3-5 contiguous stereogenic centres in a highly stereocontrolled manner. Also, the present endeavour includes the first total synthesis of scabrol A.

Application of Cp2TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes

An expedient approach toward the unified total syntheses of (+)-iridomyrmecin, (-)-isoiridomyrmecin, (+)-7-epi-boschnialactone, (+)-teucriumlactone, and (-)-dolichodial in chirally pure forms starting from readily available (+)-β-citronellene is delineated combining step economy and simplicity. Highlights include a Ti(III)-mediated reductive epoxide opening-cyclization for the construction of the core cyclopenta[c]pyran skeleton of the iridoid lactones with complete diastereoselectivity for the newly created bridgehead stereogenic centers. Subsequent transformations facilitate a short access to (+)-teucriumlactone and (-)-dolichodial and formal access to potentially other iridoids.

Biorational synthesis of iridomyrmecin diastereomers from catnip oil

4S,4aS,7S,7aR; 4R,4aS,7S,7aR; 4S,4aS,7S,7aS, and 4R,4aS,7S,7aS diastereomers of iridomyrmecin have been prepared in 5 steps from 4aS,7S,7aR and 4aS,7S,7aS-nepetalactones, major components of catnip oil. 4S,4aS,7S,7aR and 4R,4aS,7S,7aR-iridomyrmecin have b

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

Following our earlier approach to the synthesis of dihydronepetalactones, all eight stereoisomers of trans-fused iridomyrmecins were synthesized starting from the enantiomers of limonene. Combined gas chromatography and mass spectrometry including enantioselective gas chromatography revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain (4S,4aR,7S,7aR)-iridomyrmecin of 95-97% ee and stereochemically pure (4S,4aS,7R,7aS)-iridomyrmecin as a minor component.

Scope and applications of second generation palladium-catalyzed cycloalkenylation. Stereoselective total syntheses of isoiridomyrmecin, isodihydronepetalactone, and α-skytanthine

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.

A divergent approach to the diastereoselective synthesis of several ant-associated Lridoids

(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.

Stereocontrolled formation of three contiguous stereogenic centers by free radical cyclization - synthesis of (+)-iridomyrmecin and (-)-iso-iridomyrmecin - formal synthesis of δ-skythantine

A synthesis of (+)-iridomyrmecin (1), a naturally occurring insecticide with antibiotic properties, via free radical cyclization is described. In this key step, three contiguous stereogenic centers are generated with a high level of stereo-control. Wiley-

A novel route to iridoids: Enantioselective syntheses of isoiridomyrmecin and α-skytanthine

Enantio- and diastereoselective syntheses of the iridoids (-)-isoiridomyrmecin and (+)-α-skytanthine from a common intermediate (6-bromo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one) were achieved. Key steps in both syntheses are conjugated nucleophilic substitutions (SN2′ anti-reactions) with C1 zinc cyanocu-prates.

Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols

The preparation and lithium amide-induced rearrangements of 1,2-dideuterated 4-substituted cyclopentene oxides 11 and 19 are described, providing insight into the deprotonation mechanisms operating in such systems. Highly enantioselective syntheses of 4-substituted cis-4-hydroxymethylcyclopent-2-en-1-ols 32a-c are described. Also described are asymmetric syntheses of prostaglandin precursor 40 and (+)-iridomyrmecin (48) via highly enantioselective rearrangement of the epoxide 3 and subsequent Ireland-Claisen rearrangement. The Royal Society of Chemistry 1999.