17957-87-8Relevant articles and documents
Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereoselective synthesis of iridoid natural products
Chavez, David E.,Jacobsen, Eric N.
, p. 2563 - 2565 (2003)
(Matrix presented) Iridoid natural products 1-4 are accessed stereoselectively by means of tridentate (Schiff base)Cr(III)-catalyzed hetero-Diels-Alder reactions between ethyl vinyl ether and enantioenriched 5-methyl-1-cyclopentene-1-carboxaldehyde. An efficient route to the aldehyde from citronellal is afforded by the ring-closing metathesis reaction.
A Free-Radical and Protecting-Group-Free Approach to (-)-Boschnialactone and γ-Lycorane
Basante-Avenda?o, Alberto,Guerra-Ayala, Víctor E.,Sánchez-Eleuterio, Alma,Cordero-Vargas, Alejandro
, p. 2207 - 2213 (2019)
The protecting-group-free (PGF) and free-radical-based synthesis of two structurally different natural products, (-)-boschnialactone and γ-lycorane, is reported. The key step in both syntheses is a radical-ionic sequence for construction of the principal structure (a six-membered lactone and a 1,4-dicarbonyl compound, respectively), allowing short and rapid access to these natural products through a PGF route.
Intramolecular Horner-Wadsworth-Emmons reaction in base sensitive substrates: Enantiospecific synthesis of iridoid monoterpene lactones
Nangia,Prasuna,Bheema Rao
, p. 3755 - 3758 (1994)
The cyclopentapyranones (-)-7 and (-)-13, representing the cis-fused 9- carbon core of iridoid lactones, are synthesised from (+)-pulegone.
Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: An intramolecular Pauson-Khand reaction based one-stop synthetic solution
Salam, Abdus,Ray, Sayan,Zaid, Md. Abu,Kumar, Dileep,Khan, Tabrez
, p. 6831 - 6842 (2019/07/22)
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.
Formal synthesis of (±)-hop ether, (±)-isoboonein, and (±)-iridomyrmecin
Chang, Meng-Yang,Hsu, Ru-Ting,Lin, Chun-Yu,Chen, Bor-Fong,Lin, Shiang-Tsern,Chang, Nein-Chen
, p. 271 - 282 (2007/10/03)
A general synthesis of (±)-hop ether (5), (±)-isoboonein (6), and (±)-iridomyrmecin (7) from bicyclo[2.2.1]ketone (9) is described. Cyclopentenoid aldehyde (10) and bicyclo[3.2.1]lactone (11) are the key intermediates.
A novel route to iridoids: Enantioselective syntheses of isoiridomyrmecin and α-skytanthine
Ernst, Martin,Helmchen, Guenter
, p. 1953 - 1955 (2007/10/03)
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.
Total synthesis of (±)-boschnialactone and (±)-tetrahydroanhydrodesoxyaucubigenin
Chang, Meng-Yang,Lin, Ching-Han,Lee, An-Yang,Tai, Huo-Mu,Chang, Nein-Chen
, p. 205 - 210 (2007/10/03)
A total synthesis of (±)-boschnialactone (1) and (±)-tertahydroanhydrodesoxyaucubigenin (2) is described and trisubstitued cyclopentenoid 3 is a key intermediate.
Preparation of a Promising Cyclobutanone Chiral Building Block: Its Stereochemistry and Utilization
Taniguchi, Takahiko,Goto, Yasuo,Ogasawara, Kunio
, p. 707 - 709 (2007/10/03)
A cyclobutanone possessing a bicyclo[2.2.1]heptene framework {endo-tricyclo[4.2.1.02,5]non-7-en-3-one} has been prepared in both enantiomeric forms employing lipase-mediated kinetic resolution as the key step. To determine the absolute configuration, as well as to demonstrate the synthetic potential, both enantiomers of the cyclobutanone obtained have been transformed enantioconvergently into the key intermediate of the sesquiterpene (+)-β-santalene and the iridoid monoterpene (-)-boschnialactone.
Total Synthesis of (±)-Patriscabrol and (±)-Boschnialactone
Chiu, Jiun-Yuh,Chiu, Chih-Tsao,Chang, Nein-Chen
, p. 59 - 63 (2007/10/03)
A total synthesis of (±)-patriscabrol (1) and (±)-boschnialactone (2) is described. The cyclopentapyranone skeleton is assembled by means of Baeyer-Villiger oxidation of ketol 5.
Syntheses of several cyclopentano-monoterpene lactones using 1,3-dioxin vinylogous ester
Ohba,Haneishi,Fuji
, p. 26 - 31 (2007/10/02)
Formal syntheses of (±)-boschnialactone (5) and three cyclopentano-monoterpene lactones [i.e., (±)-(iridomyrmecin (6), (±)-isoiridomyrmecin (7), and (±)-allodolicholactone (8)] have been accomplished in the form of the syntheses of 2-(methoxymethyl)-3-methyl-2-cyclopenten-1-one (11) and (±)-(4aα,7α,7aα)-hexahydro-7-methylcyclopenta[c]pyran-3(1H)-one (19), respectively, starting from 6,7-dihyd;ocyclopenta-1,3-dioxin-5(4H)-one (2). A synthesis of (±)-isodehydroiridomyrmecin (9) has also been achieved through a route including direct substitution of the hydroxy group of 2-(tert-butyldimethylsilyloxymethyl)-3- methyl-2-cyclopenten-1-ol (22) with 1-(tert-butyldimethylsilyloxy)-1-methoxyethene (23) as a key step.
