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T1 - Asymmetric synthesis of chiral tetraphenylenes

AB - Short, efficient pathways are described for the synthesis of racemic 2-nitroimidazole radiation sensitizer RB-6145 (2a) and each of its corresponding (R)- and (S)-enantiomers (2b and 2c, respectively). The synthesis of each enantiomer commences with the appropriate chiral epichlorohydrin and utilizes a novel application of 3-trimethylsilyl-2-oxazolidinone (3b) as a mild, safe surrogate for highly toxic aziridine. The synthesis of the (R)-enantiomer (2b) has been successfully scaled up to provide multi-kilo quantities of material for early stage preclinical evaluation.

N2 - Short, efficient pathways are described for the synthesis of racemic 2-nitroimidazole radiation sensitizer RB-6145 (2a) and each of its corresponding (R)- and (S)-enantiomers (2b and 2c, respectively). The synthesis of each enantiomer commences with the appropriate chiral epichlorohydrin and utilizes a novel application of 3-trimethylsilyl-2-oxazolidinone (3b) as a mild, safe surrogate for highly toxic aziridine. The synthesis of the (R)-enantiomer (2b) has been successfully scaled up to provide multi-kilo quantities of material for early stage preclinical evaluation.

T1 - Chiral synthesis of (-)-mesembranol starting from D-glucose

The chiral resolving agentcan also be recovered for re-use.

T1 - Microfluidic synthesis of chiral salen Mn(ii) and Co(ii) complexes containing lysozyme

N2 - The chiral synthesis of the Sceletium alkaloid, (-)-mesembranol 1 is described; the cyclohexane ring in 1 is prepared in an optically active form from D-glucose using Ferrier's carbocyclisation reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.

AB - The chiral synthesis of the Sceletium alkaloid, (-)-mesembranol 1 is described; the cyclohexane ring in 1 is prepared in an optically active form from D-glucose using Ferrier's carbocyclisation reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.

Epoxide synthesis by ring closure - Organic Chemistry

AB - The chiral synthesis of the immunosuppressive sesquiterpene, FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd- catalyzed Stille coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814.

Following this separation the chiral resolving agent rcan be removed by through some chemical reaction to give the two separate enantiomers.

Efficient microfluidic synthesis of chiral salen Mn(ii) and Co(ii) complexes containing lysozyme was achieved. The reaction conditions for the delicate protein were controlled precisely with a separation barrier in the microfluidic device. The microfluidic method has the following advantages over the conventional method: a remarkable reduction in the reaction time from 4.5 h to less than 1 s for the synthesis of Mn(ii) and Co(ii) complexes, a reduction in the reaction temperature from 40 to 23 °C, and no need for an N2 atmosphere because all the reagents are isolated from the air. A three-fold yield improvement was achieved for Mn(ii) and Co(ii) complexes containing lysozyme compared with conventional synthesis.

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Synthesis of O -Heterocycles - Organic Chemistry Portal


Chiral Molecules - Custom Chemical Synthesis

Enzymes are particularly effective in making this distinction, so that a racemic mixture can often be easily resolved by reaction with some simple substance in the presence of the chiral enzyme as catalyst.

Chiral pool synthesis + examples - YouTube

The two enantiomers present in a racemic mixtrue can be reacted with a pure enantiomer of a chiral compound (called a resolving agent) which we have on hand (many occur in pure form in nature).

Chapter 8 – Synthesis of axially chiral biaryls

Since both enantiomers have equal energy, and since there is nothing in the catalyst or solvent or reactant that is chiral, both enantiomers are formed in equal amounts(for a mechanistic explanation, see later).

Chiral pool synthesis - WikiVisually

N2 - The chiral synthesis of the immunosuppressive sesquiterpene, FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd- catalyzed Stille coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814.

Asymmetric synthesis of chiral tetraphenylenes - Elsevier

The chiral synthesis of the Sceletium alkaloid, (-)-mesembranol 1 is described; the cyclohexane ring in 1 is prepared in an optically active form from D-glucose using Ferrier's carbocyclisation reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.

Chiral synthesis - WikiVisually

The chiral synthesis of the immunosuppressive sesquiterpene, FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd- catalyzed Stille coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814.

T1 - A versatile synthesis of planar chiral ligands

AB - (Chemical Equation Presentation) Intriguing scaffolds: Tetraphenylenes with symmetry-breaking substitution have chiral π systems and extraordinarily high barriers for racemization. Their applications as building blocks for chiral materials and as ligands in asymmetric syn-thesis are hindered by the difficulty in obtaining the chiral tetraphenylene core. Rhodium-catalyzed [2+2+2] cycloadditions of triynes provide an effective alternative synthesis.

Epoxide synthesis by epoxidation - Organic chemistry

N2 - Efficient microfluidic synthesis of chiral salen Mn(ii) and Co(ii) complexes containing lysozyme was achieved. The reaction conditions for the delicate protein were controlled precisely with a separation barrier in the microfluidic device. The microfluidic method has the following advantages over the conventional method: a remarkable reduction in the reaction time from 4.5 h to less than 1 s for the synthesis of Mn(ii) and Co(ii) complexes, a reduction in the reaction temperature from 40 to 23 °C, and no need for an N2 atmosphere because all the reagents are isolated from the air. A three-fold yield improvement was achieved for Mn(ii) and Co(ii) complexes containing lysozyme compared with conventional synthesis.

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