121541-65-9Relevant academic research and scientific papers
Cross-Metathesis Approach to the Tricyclic Marine Alkaloids (-)-Fasicularin and (-)-Lepadiformine A
Burnley, James,Wang, Zhen J.,Jackson, W. Roy,Robinson, Andrea J.
, p. 8497 - 8505 (2017/08/23)
A cross-metathesis protocol has been developed to provide facile access to highly hindered trisubstituted α-branched olefins, which when coupled with a cationic azaspirocyclization reaction, generates the marine alkaloids (-)-fasicularin 2 and a pro-forma synthesis of (-)-lepadiformine A 1.
Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes
Fang, Lichao,Yan, Lu,Haeffner, Fredrik,Morken, James P.
supporting information, p. 2508 - 2511 (2016/03/12)
Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts. Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates.
Catalytic Enantioselective Peroxidation of α,β-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides
Hu, Lin,Lu, Xiaojie,Deng, Li
supporting information, p. 8400 - 8403 (2015/07/15)
We have developed an unprecedented highly enantioselective catalytic peroxidation of enals. Critical to this development is the discovery that varying the structure of the hydroperoxide has a significant impact on the enantioselectivity of the organocatal
Organocatalysis in natural product synthesis: A simple one-pot approach to optically active β-diols
Andersen, Nikolaj Rojkjaaer,Hansen, Signe Grann,Bertelsen, Soren,Jorgensen, Karl Anker
experimental part, p. 3193 - 3198 (2010/04/28)
Optically active β-diols have been prepared using an organocatalytic one-pot approach from α,β-unsaturated aldehydes using (E)-benzaldehyde oxime as nucleophile in an oxa-Michael reaction with subsequent in situ reduction or Grignard addition. With this p
Ozonolysis of ricinolic acid derivatives and transformations of the ozonolysis products under barton reaction conditions
Ishmuratov,Kharisov,Shayakhmetova,Botsman,Shitikova,Tolstikov
, p. 643 - 649 (2008/02/01)
The possibility of functionalizing the alkyl part of ricinolic acid using the Barton reaction was investigated.
Opening of Substituted Oxetanes with H2O2 and Alkyl Hydroperoxides: Stereoselective Approach to 3-Peroxyalcohols and 1,2,4-Trioxepanes
Dussault, Patrick H.,Trullinger, Tony K.,Noor-e-Ain, Farhana
, p. 4591 - 4593 (2007/10/03)
(Equation Presented) Lewis acid-catalyzed opening of oxetanes by hydrogen peroxide proceeds regioselectively and with good to moderate stereoselectivity to furnish enantiomerically enriched 3-hydroperoxyalkanols. The corresponding opening using alkyl hydroperoxides furnishes 3-peroxyalkanols. The hydroperoxyalkanols are easily converted into enantiomerically enriched 1,2,4-trioxepanes, building blocks for antimalarials.
Application of Microbial Enantiofacially Selective Hydrolysis in Natural Product Synthesis
Katoh, Osamu,Sugai, Takeshi,Ohta, Hiromichi
, p. 1935 - 1944 (2007/10/02)
Pichia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70percent yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87percent e.e.), to be the starting material for the synthesis of optically active natural products.Methyl (R)-3-hydroxy-12-methyltridecanoate, a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation.Final products were enantiomerically enriched to 94-95percent e.e., by the lipase-mediated enantioselective transesterification, which could remove the minor enantiomer as the corresponding acetate.
Chemistry of Fruit Flies. Composition of the Rectal Gland Secretion of (Male) Dacus cucumis (Cucumber Fly) and Dacus halfordiae. Characterization of (Z,Z)-2,8-Dimethyl-1,7-dioxaspiroundecane
Kitching, William,Lewis, Judith A.,Perkins, Michael V.,Drew, Richard,Moore, Christopher J.,et al.
, p. 3893 - 3902 (2007/10/02)
Combined gas chromatography-mass spectrometry and synthesis have established that the major components of the rectal gland secretion of adult male cucumber flies (Dacus cucumis) are the E,E, E,Z, and Z,Z diastereomers of 2,8-dimethyl-1,7-dioxaspiroundecane, which have been synthesized utilizing organomercury chemistry from 1,10-undecadien-6-one.The thermodynamically least stable Z,Z diastereomer has been characterized for the first time, by 1H and 13C NMR measurements and mass spectrometry.Minor amounts of 3-hydroxy-2,8-dimethyl-1,7-dioxaspiroundecane and various derivatives of the 1,6-dioxaspirodecane and 1,7-dioxaspirododecane systems are also present. 1,3-Nonanediol occurs in significant amounts, and both enantiomers have been acquired by Sharpless asymmetric epoxidation of (E)-2-nonen-1-ol followed by Red-Al (Aldrich) reduction of the chiral epoxy alcohols.Chiral gas chromatographic analysis of the diols (as their cyclic carbonates) has demonstrated that the natural material is the R-(-) enantiomer.Natural (E,Z)-2,8-dimethyl-1,7-dioxaspiroundecane is shown to be racemic, whereas the more abundant E,E diastereomer is enantiomerically highly pure, possessing the 2S,6R,8S configuration.The major volatile component of the rectal gland secretion of male Dacus halfordiae (Tryon) is also (E,E)-2,8-dimethyl-1,7-dioxaspiroundecane, with no detectable levels of the E,Z or Z,Z isomers.Other spiroacetals present were 2-ethyl-7-methyl-1,6-dioxaspirodecane and the unusual even carbon-numbered (E,E)-2-ethyl-8-methyl-1,7-dioxaspiroundecane. 6-Oxo-1-nonanol, diethyl succinate, and 2-methyl-6-pentyl-3,4-dihydro-2H-pyran were also identified.
