One-pot synthesis of cage alcohols

Klimochkin, Yu. N.; Yudashkin, A. V.; Zhilkina, E. O.; Ивлева, Е. А.; Моисеев, И. К.; Oshis, Ya. F.

doi:10.1134/s1070428017070028

Cited by 24 publications

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“…Inspired by previous works of Klimochkin and coauthors, we have expanded their method by adding one more nitroxylation step without isolating the product. We used this one-pot protocol to synthesize 3-hydroxy-5-methyladamantane-1-carboxylic acid (step i, Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…The literature approach to a key precursor for (1S,3R,5R,7S)-trans-N-(4-aminocyclohexyl)-3-methyl-5-phenyladamantane-1-carboxamide synthesis�racemic 3-methyl-5phenyladamantane-1-carboxylic acid (rac-7) is based on the stepwise introduction of functional groups to the methyladamantane core (Scheme 2). Inspired by previous works of Klimochkin and coauthors, 35 we have expanded their method by adding one more nitroxylation step without isolating the product. We used this one-pot protocol to synthesize 3-hydroxy-5-methyladamantane-1-carboxylic acid (step i, Scheme 3).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Scale-Up Synthesis of 1-Methyladamantane and Its Functionalization as a Key Point for Promising Antiviral Agents

Pashenko

Gaidai

Hryhoriev

et al. 2023

Org. Process Res. Dev.

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Methyladamantane and its derivatives are rare chemotypes for industrial and even wide research use. The proposed scalable and inexpensive approach to such compounds opens the door to further extensive study of biologically active derivatives based on this uncommon core. Optimized synthesis of the key precursor, the chiral (1S,3R,5R,7S)-3-methyl-5-phenyladamantane-1carboxylic acid, showcases some significant innovations. The main one is very effective and cost-efficient stacked injections in preparative chiral chromatography and showed potential for enantioresolution of chiral cage compounds. Scaling the preparation of (1S,3R,5R,7S)-trans-N-(4-aminocyclohexyl)-3-methyl-5-phenyladamantane-1-carboxamide, which was recently shown to have notable activity against the Ebola virus, to multigram levels is an excellent example of our elaboration significance. It may push forward further biological investigation of this promising antiviral agent.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%