132260-32-3Relevant academic research and scientific papers
Stereospecific synthesis of (E,Z)- and (Z,Z)-hexadeca-10,12-dienal. Sex pheromone components of Diaphania hyalinata
Cabezas, Jorge A.,Oehlschlager, Allan C.
, p. 107 - 111 (1999)
Isomeric (E,Z)- and (Z,Z)-hexadeca-10,12-dienal were prepared, stereospecifically, in 51% and 43% overall yields from dec-1-yne.
Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide
Hikosaka, Gen,Hattori, Yasunao,Makabe, Hidefumi
, p. 1367 - 1371 (2014)
The syntheses of (+)- and (-)-akolactone B and (+)-ancepsenolide were accomplished using a Pd-catalyzed carbonylation. As to the absolute configuration of akolactone B, making a comparison of the specific rotation of both enantiomers of synthetic akolactone B and the natural compound suggests that the absolute configuration at the 4-position of akolactone B is (R).
Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis
Yu, Peng,Bismuto, Alessandro,Morandi, Bill
supporting information, p. 2904 - 2910 (2020/01/25)
Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group tolerance and safety profile of these reactions compared to the state-of-the-art. This method has granted access to alkenyl halide compounds containing acid-sensitive groups, such as tertiary alcohols, silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram-scale synthesis where low catalyst loading was achieved.
Hydration of terminal alkynes catalyzed by water-soluble cobalt porphyrin complexes
Tachinami, Tadashi,Nishimura, Takuho,Ushimaru, Richiro,Noyori, Ryoji,Naka, Hiroshi
supporting information, p. 50 - 53 (2013/02/23)
Water-soluble cobalt(III) porphyrin complexes were found to promote the hydration of terminal alkynes to give methyl ketones. The alkyne hydration proceeded in good to excellent yield with 0.1 to 2 mol % cobalt catalyst 1 and was compatible with the presence of acid/base- or redox-sensitive functional groups such as alkyl silyl ethers; allyl ethers; trityl ethers; benzyl ethers; carboxylic esters; boronic esters; carboxamides; nitriles; and nitro, iodo, and acetal groups. Some of the alkyne substrates tested here are otherwise difficult to hydrate. The alkyne hydration can be performed on a gram scale, and the catalyst can be recovered by aqueous workup.
Investigation of the origin and synthetic application of the pseudodilution effect for Pd-catalyzed macrocyclisations in concentrated solutions with immobilized catalysts
Brehm, Elisabeth,Breinbauer, Rolf
supporting information, p. 4750 - 4756 (2013/07/26)
Immobilized Pd-complexes allowed macrocyclisations via the Tsuji-Trost-reaction in concentrated solutions. Systematic studies suggest that the origin of this pseudodilution effect is neither film diffusion nor gel diffusion, but the reduction in conformational freedom of intermediates and intramolecular prenucleophile activation. In contrast a pseudodilution effect could not be observed for Sonogashira- and Suzuki-macrocyclisations.
Total synthesis of two photoactivatable analogues of the growth-factor-like mediator sphingosine 1-phosphate: Differential interaction with protein targets
Lu, Xuequan,Cseh, Sandor,Byun, Hoe-Sup,Tigyi, Gabor,Bittman, Robert
, p. 7046 - 7050 (2007/10/03)
The first synthesis of two photoreactive analogues of the lipid mediator and second messenger sphingosine 1-phosphate (S1P), [32P]-labeled (2S,3R)-14-O-(4′-benzoylphenyl)- and (2S,3R)-14-O-((4′ -trifluoromethyldiazirinyl)phenyl)-(4E) -tetradece
Synthesis of β-Resorcylic Macrolides via Organopalladium Chemistry. Application to the Total Synthesis of (S)-Zearalenone
Kalivretenos, A.,Stille, J. K.,Hegedus, L. S.
, p. 2883 - 2894 (2007/10/02)
The β-resorcyclic macrolides are a class of naturally occurring 12- and 14-membered macrolides.Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest.In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct β-resorcylic macrolides.The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones.This methodology was then used to prepare (S)-zearalenone (1).
