53750-52-0Relevant articles and documents
SECO-AMBRAKETALS
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, (2022/04/03)
The present invention primarily relates to compounds of formula (I) and compositions comprising one, two, three or more compound(s) of formula (I) or consisting of two, three or more compound(s) of formula (I). The invention further relates to methods for producing a compound of formula (I) or a composition as defined herein, the use of a compound of formula (I) as defined herein as a fragrance substance, the use of a composition as defined herein as a fragrance substance mixture and the use of a compound of formula (I) or a composition as defined herein for imparting, modifying and/or enhancing one or more olfactory notes selected from the group consisting of the notes ambergris, woody and animalic. Moreover, the present invention relates to fragrance substance compositions and perfumed products as defined herein, methods for producing a perfumed product, methods for perfuming a product and methods for perfuming hair, skin, textile fibres, surfaces and/or ambient air.
Skeletal and stereochemical diversification of tricyclic frameworks inspired by Ca2+-ATPaSe inhibitors, artemisinin and transtaganolide D
Oguri, Hiroki,Yamagishi, Yutaka,Hiruma, Takahisa,Oikawa, Hideaki
supporting information; experimental part, p. 601 - 604 (2009/09/25)
(Chemical Equation Presented) Inspired by the common skeletal motifs of Ca2+-ATPases inhibitors involving artemisinin and transtaganolide D, small molecule collections with the three-dimensional structural diversity of tricyclic systems were designed and expeditiously synthesized (4-5 steps). A synthetic strategy featuring stereochemical diversification of ring-junctions and control of cyclizatlon modes was devised to access varied molecular architectures in a systematic fashion.
Synthetic studies toward jatrophane diterpenes from Euphorbia characias. enantioselective synthesis of (-)-15-O-Acetyl-3-O-propionyl-17-norcharaciol
Helmboldt, Hannes,Hiersemann, Martin
scheme or table, p. 1698 - 1708 (2009/10/02)
The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.
Synthesis of the norjatrophane diterpene (-)-15-acetyl-3-propionyl-17- norcharaciol
Helmboldt, Hannes,Koehler, Daniel,Hiersemann, Martin
, p. 1573 - 1576 (2007/10/03)
A scalable enantioselective synthesis of the nonnatural 17-norjatrophane diterpene 3-propionyl-15-acetyl-17-norcharaciol is described. Key C/C-connecting transformations are an Evans aldol reaction, an intramolecular carbonyl ene reaction, a Horner-Wadsworth-Emmons olefination, and a ring-closing metathesis for the formation of a 12-membered carbacycle.
Catalytic and stoichiometric Lewis acid participation in aldehyde ene cyclisations
Braddock, D. Christopher,Brown, John M.
, p. 741 - 756 (2007/10/03)
Racemic 2-isopropyl-2-methylhex-5-enal has been synthesised in order to probe ene cyclisations leading to menthol analogues. The objective was first to discover catalytic conditions for preferential cyclisation to the menthol rather than the neomenthol series and then to develop (dynamic) kinetic resolution procedures which afforded a single enantiomer of product. It was found that catalytic quantities of both Me2AlCl and a bulky methyl-aluminium bis(phenoxide) reagent gave products attributed to a Meerwein-Pondorff-Verley reaction. In this the aldehyde is reduced to a primary alcohol and the ene product oxidised to the corresponding α,β-unsaturated ketone. By contrast, a related bulky chloroaluminium reagent catalysed the ene cyclisation cleanly, but preferentially to the undesired neomenthyl stereoisomer.
Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis, enantioselective total synthesis of Sch 38516 (fluvirucin B1)
Xu, Zhongmin,Johannes, Charles W.,Houri, Ahmad F.,La, Daniel S.,Cogan, Derek A.,Hofilena, Gloria E.,Hoveyda, Amir H.
, p. 10302 - 10316 (2007/10/03)
The first enantioselective total synthesis of antifungal agent Sch 38516, also known as fluvirucin B1, is described. The synthesis includes a convergent asymmetric preparation of amine 17 and acid 18, which are then united to afford diene 62. Metal-catalyzed transformations play a crucial role in the synthesis of the latter moiety. Of particular note are the diastereo- and enantioselective Zr-catalyzed alkylations, a tandem Ti- and Ni-catalyzed process that constitutes a hydrovinylation reaction, and a Ru-catalyzed alcohol oxidation to afford carboxylic acid 18. The requisite carbohydrate 38 is synthesized in a highly diastereo- and enantioselective fashion. Optical purity of the carbohydrate moiety arises from the use of the asymmetric dihydroxylation method of Sharpless; diastereochemical control is achieved through a selective dipolar [3 + 2] cycloaddition with a readily available amine serving as the chiral auxiliary. Union of the appropriately outfitted carbohydrate 71 and diene 62 through an efficient and diastereoselective glycosylation is followed by a remarkably efficient Mo-catalyzed macrocyclization that proceeds readily at room temperature.
Synthesis of pyrrolidines and piperidines via palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides
Larock,Yang,Weinreb,Herr
, p. 4172 - 4178 (2007/10/02)
The palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides affords good yields of 2-(1-alkenyl)pyrrolidine and -piperidine sulfonamides via vinylpalladium addition to the olefin, regioselective rearrangement to a π-allylpalladium intermediate, and subsequent intramolecular nucleophilic displacement of palladium.
The synthesis of the isomeric components of San Jose scale pheromone - An illustration of a stereospecific synthesis of trisubstituted alkenes
Alderdice,Spino,Weiler
, p. 1955 - 1963 (2007/10/02)
The three isomeric components of the San Jose scale pheromone, 5-7, have been synthesized from a common β-keto ester intermediate. A study of the alkylation of the dianion of methyl acetoacetate with a series of alkylating agents with the same carbon skeleton has been carried out. The trisubstituted alkenes in 5 and 6 have been synthesized stereospecifically via a copper-catalyzed coupling of a methyl Grignard reagent with the E or Z enol phosphate from the alkylated β-keto ester. In the case of the Z enol derivative, the coupling reaction was carried out on the diethyl- and diphenylphosphates, and the enol triflate. The diethyl enol phosphate gave the highest stereoselectivity. The synthetic pheromones were attractive to San Jose scale in the field.
STEREOSELECTIVE REDUCTION OF ACETALS. A METHOD FOR REDUCTIVE GENERATION OF HETEROCYCLIC RING SYSTEMS
Ishihara, Kazuaki,Mori, Atsunori,Yamamoto, Hisashi
, p. 4595 - 4612 (2007/10/02)
A new synthetic process for the construction of oxygen-containing heterocyclic systems starting from bicyclic acetals is described.We have investigated the mechanism and the stereochemical course of the reductive cleavage of acetals.
