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M.; Yus, M., Asymmetric ring opening of epoxides.

AB - The stereoselective total synthesis of garsubellin A is described. The total synthesis was achieved through the stereoselective construction of a bicyclo3.3.1nonane derivative via a three-step sequence: intramolecular cyclopropanation, formation of a germinal dimethyl group, and regioselective ring opening of cyclopropane. To complete the total synthesis of garsubellin A, chemo-And stereoselective hydrogenation to generate the C8 stereogenic center is followed by the formation of the fused tetrahydrofuran ring by a regioselective epoxide-opening reaction with C3 ketone, and finally cross metathesis to construct two prenyl groups.

The image above shows the synthesis of an alcohol from a ketoneby reduction.

An example of a more rmote effect is seen below, where stereoselective epoxidation of the double is believed to be directed to the bottom face of the alkene by the hydroxyl group in the conformation shown. Synthesis of Cycloepoxydon: Li, C.; Pace, E. A.; Liang, M.-C.; Lobkovsky, E.; Gilmore, T. D. Porco, J. A. 2001, , 11308.

H., His6 tag-assisted chemical protein synthesis.

Living Radical Polymerization as a Tool for the Synthesis of Polymer-Protein/Peptide Bioconjugates.

Ketones, carboxylic esters, carboxylic acids, and carboxamides can in general be converted to enolates by deprotonation with strong bases like lithium diisopropylamide. The enolates can also be formed by conjugate reduction reactions. The enolates react usefully with SN2-reactive alkyl halides, aldehydes, acylating agents, and Michael acceptors, as well as other electrophiles. Aldehyde enolates cannot usually be prepared and used in this way because self-condensation is too fast. The enolates of acid chlorides and acid anhydrides are unstable - they eliminate chloride or acetate to form ketenes.

Epoxides and secondary halides can sometimes be used, but their SN2 reactions with enolates are often too slow to compete with side reaction like elimination of halide to alkene or enolate equilibration (for ketone enolates) and decomposition (for ester enolates).

J., Spirodiepoxides in Total Synthesis: Epoxomicin.

M., Synthesis of bio-inspired hybrid polymers using peptide synthesis and protein engineering.

J.; Buerkstuemmer, E.; Linclau, B., Short Synthesis of Enantiopure 2-Symmetric 1,2:4,5-Diepoxypentane and "Pseudo"-2-Symmetric 3-Azido-1,2:4,5-diepoxypentane from Arabitol.

F., III, Towards organo-click chemistry: Development of organocatalytic multicomponent reactions through combinations of Aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions.

W., Protein semi-synthesis: New proteins for functional and structural studies.
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An epoxide is a cyclic ether with a three-atom ring

The Baeyer-Villiger oxidation involves the peroxide-induced insertion of an oxygen between the carbonyl carbon and one of the substituents to form an ester (or a lactone if the ketone was cyclic, as in the example below) through the action of a hydroperoxy oxidant, usually a percarboxylic acid, but hydrogen peroxide itself under acid or base-catalyzed conditions will sometimes be reactive enough for aldehydes or if the ketone is strained (e.g. cyclobutanones).

Epoxide synthesis by epoxidation - Organic chemistry

However, there are many exceptions to this sequence depending on the reagents used, as well as steric and electronic effects in the substrate. In addition to peracids, alkaline hydrogen peroxide or hydrogen peroxide together with a Bronsted or Lewis acid like BF3 can also be effective. The migratory tendency can be quite different with different reagents. For example, benzaldehyde gives mostly H migration with KHSO5, mostly Ph migration with H2O2/NaOH, and about equal amounts of both with MCPBA. Electron rich aryl rings migrate preferentially over electron poor ones, and thus the sequence among secondary, aryl, and hydrogen migratory aptitudes can be changed by substituents on the aromatic ring. Vinyl groups migrate comparably to aryl, but the enol ester products are often epoxidized during the reaction.

Epoxide synthesis by ring closure - Organic Chemistry

A common source for producing alcohols is from carbonylcompounds. The choice of carbonyl type (ketone, aldehyde, ester,etc) and the type of reaction (Grignard addition or Reduction),will determine the product(s) you will get. Fortunately, there area number of variations of carbonyls, leading to a number of choicesin product.

MS 918 - Epoxide and Ether Practice | MendelSet

There is a useful stereochemical effect in the peroxidation of certain allylic alcohols, which is also sometimes seen for alkenes with more remote hydroxyl groups, called the Henbest effect (Henbest, H. B.; Wilson, R. A. I. . 1957, 1958.) - the hypothesis is that the peracid hydrogen bonds to the hydroxyl group, and this leads to stereochemical control in the epoxidation. A typical example is shown below from a synthesis of Hemibrevetoxin B: Zakarian, A.; Batch, A.; Holton, R. A.. 2003, , 7822-7823.

MS 918 - Epoxide and Ether Practice

Metalloenamines also provide a means for attaching a chiral auxiliary. Below an example of an application of the widely-used SAMP hydrazone for an asymmetric aldehyde alkylation. Synthesis of Imperanene: Shattuk, J. C.; Shreve, C. M.; Solomon, S. E. 2001, , 3021.

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