2088-07-5

Usage

InChI:InChI=1/C6H12O/c1-4-6(7)5(2)3/h6-7H,2,4H2,1,3H3/t6-/m0/s1

Upstream product

• 78-85-3 2-methylpropenal 
• 925-90-6 ethylmagnesium bromide 
• 1838-89-7 rac-2-methylpent-1-en-3-yl acetate 
• 74-96-4 ethyl bromide 
• 763-29-1 2-Methyl-1-pentene 
• 625-27-4 2-methyl-2-pentene 
• 2564-18-3 1-phenyl-3-((dimethylamino)styryl)-5-((dimethylamino)phenyl)-2-pyrazoline 
• 4104-01-2 3-Chlor-2-methylpent-1-en 
• 96455-85-5 1,3,2-dioxaphospholane 
• 7795-80-4 2-methylpentane-2,3-diol 
• 13291-18-4 isopropenylmagnesium bromide 
• 123-38-6 propionaldehyde 
• 592-43-8 2-hexene 
• 557-20-0 diethylzinc 

Downstream Products

• 84599-41-7 (R^*,S^*)-α-Ethyl-2-methyloxiranemethanol 
• 125637-07-2 (R)-3-hydroxy-2-methylpent-1-ene 
• 76919-85-2 1-(2-Methyl-oxiranyl)-propan-1-one 
• 98168-21-9 (S)-(-)-2-methyl-1-penten-3-ol 
• 67054-00-6 (+)-pumiliotoxin A 
• 139079-93-9 (R)-2-methylpent-1-en-3-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 

Relevant academic research and scientific papers

CHEMISTRY OF SINGLET OXYGEN. PART 44: MECHANISM OF PHOTOOXIDATION OF 2,5-DIMETHYLHEXA-2,4-DIENE AND 2-METHYL-2-PENTENE.

Solvent and temperature effects on the singlet oxygen oxidations of 2,6-dimethyl-2,4-hexadiene (DMHD) and 2-methyl-2-pentene (2M2P) are studied. It is concluded that the initial interaction between 2M2P and **1O//2 (which gives only ene products) and that between DMHD and **1O//2 (which gives ene products, dioxetane, and nonreactive quenching) are identical. It is also suggested that the quenching path for DMHD could involve formation of an intermediate zwitterion or 1,4-biradical, which undergoes intersystem crossing and decays to ground-state oxygen and DMHD.

Ambruticins: tetrahydropyran ring formation and total synthesis

The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.

Chromium-Catalyzed Production of Diols From Olefins

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

Large-scale preparation of key building blocks for the manufacture of fully synthetic macrolide antibiotics

Key building blocks for the production of fully synthetic macrolides have been scaled-up in first time pilot plant and kilo-lab campaigns. These building blocks have supported the discovery of new macrolide antibiotics as well as ongoing preclinical studies.

Mechanistic Insight into Palladium-Catalyzed Cycloisomerization: A Combined Experimental and Theoretical Study

The cycloisomerization of enynes catalyzed by Pd(OAc)2 and bis-benzylidene ethylenediamine (bbeda) is a landmark methodology in transition-metal-catalyzed cycloisomerization. However, the mechanistic pathway by which this reaction proceeds has remained unclear for several decades. Here we describe mechanistic investigations into this reaction using enynamides, which deliver azacycles with high regio- and stereocontrol. Extensive 1H NMR spectroscopic studies and isotope effects support a palladium(II) hydride-mediated pathway and reveal crucial roles of bbeda, water, and the precise nature of the Pd(OAc)2 pre-catalyst. Computational studies support these mechanistic findings and lead to a clear picture of the origins of the high stereocontrol that can be achieved in this transformation, as well as suggesting a novel mechanism by which hydrometalation proceeds.

Practical Protocols for the Preparation of Highly Enantioenriched Silyl Ethers of (R)-3-Hydroxypentan-2-one, Building Blocks for the Synthesis of Macrolide Antibiotics

Methacrolein is transformed in three steps to (R)-3-tert-butyldiphenylsilyloxypentan-2-one or (R)-3-tert-butyldimethylsilyloxypentan-2-one, compounds which serve as building blocks for the construction of macrolide antibiotics. The route is practical, highly enantioselective, and easily scaled.

14-MEMBERED KETOLIDES AND METHODS OF THEIR PREPARATION AND USE

Provided herein are methods of preparing new 14-membered ketolides via coupling of an eastern and western half moiety, followed by macrocyclization, and optional functionalization. Intermediates in the synthesis of these ketolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using these ketolides are also provided.

MACROLIDES AND METHODS OF THEIR PREPARATION AND USE

Provided herein are methods of preparing macrolides by the coupling of an eastern and western half, followed by macrocyclization, to provide macrolides, including both known and novel macrolides. Intermediates in the synthesis of macrolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using the inventive macrolides are also provided. A general diastereoselective aldol methodology used in the synthesis of the western half is further provided.

Asymmetric syntheses of 8-oxabicyclo[3,2,1]octanes: A cationic cascade cyclization

High octane: A novel and practical syntheses of 8-oxabicyclo[3.2.1]octanes using a cationic cascade cyclization reaction has been developed (see scheme; TIPS=triisopropylsilyl). The diastereomer of the cyclization product isolated depends upon whether the acetal or aldehyde substrate is used. Copyright

Stereoselective synthesis of conjugated trienols from allylic alcohols and 1-iodo-1,3-dienes

The stereoselective synthesis of conjugated trienes has been achieved from allylic alcohols and 1-iodo-1,3-dienes using Pd(OAc)2/AgOAc.