92344-02-0

Usage

Uses

Used in Research Applications:
Methyl (2R)-2-Methyl-5-oxocyclopentanecarboxylate is used as a research chemical for [application reason], such as studying its properties, reactivity, and potential applications in various chemical reactions.
Used in Chemical Reactions:
Methyl (2R)-2-Methyl-5-oxocyclopentanecarboxylate is used as a reactant or intermediate in [application reason], such as in the synthesis of other organic compounds or in the development of new chemical processes.
Note: Since the provided materials do not specify any significant industrial or commercial use for Methyl (2R)-2-Methyl-5-oxocyclopentanecarboxylate, the uses listed above are general and may not represent specific applications. Further research and information would be required to identify more detailed uses in different industries.

Upstream product

• 14203-46-4 4-methyl-cyclohexane-1,3-dione 
• 67-56-1 methanol 
• 122571-21-5 2-Diazo-4-methylcyclohexane-1,3-dione 
• 2005-58-5 (5R)-2-isopropylidene-5-methylcyclopentanecarboxylic acid methyl ester 
• 131190-04-0 α-diazo methyl 3-oxoheptanoate 

Downstream Products

• 205927-79-3 C₂₂H₂₉NO₃S 
• 205927-77-1 N-((3R,3aS,7R,8S)-3,9-Dimethyl-6-oxo-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide 
• 205927-78-2 N-((3R,3aS,6R,7R,8S)-6-Hydroxy-3,6,9-trimethyl-1,2,3,4,5,6,7,8-octahydro-3a,7-methano-cyclopentacycloocten-8-yl)-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

Total Synthesis and Stereochemical Assignment of Delavatine A: Rh-Catalyzed Asymmetric Hydrogenation of Indene-Type Tetrasubstituted Olefins and Kinetic Resolution through Pd-Catalyzed Triflamide-Directed C-H Olefination

Delavatine A (1) is a structurally unusual isoquinoline alkaloid isolated from Incarvillea delavayi. The first and gram-scale total synthesis of 1 was accomplished in 13 steps (the longest linear sequence) from commercially available starting materials. We exploited an isoquinoline construction strategy and developed two reactions, namely Rh-catalyzed asymmetric hydrogenation of indene-type tetrasubstituted olefins and kinetic resolution of β-alkyl phenylethylamine derivatives through Pd-catalyzed triflamide-directed C-H olefination. The substrate scope of the first reaction covered unfunctionalized olefins and those containing polar functionalities such as sulfonamides. The kinetic resolution provided a collection of enantioenriched indane- and tetralin-based triflamides, including those bearing quaternary chiral centers. The selectivity factor (s) exceeded 100 for a number of substrates. These reactions enabled two different yet related approaches to a key intermediate 28 in excellent enantiopurity. In the synthesis, the triflamide served as not only an effective directing group for C-H bond activation but also a versatile functional group for further elaborations. The relative and absolute configurations of delavatine A were unambiguously assigned by the syntheses of the natural product and its three stereoisomers. Their cytotoxicity against a series of cancer cell lines was evaluated.

Formal Total Synthesis of (-)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes

Synthetic studies toward highly oxygenated seco-prezizaane sesquiterpenes are reported, which culminated in a formal total synthesis of the neurotrophic agent (-)-jiadifenolide. For the construction of the tricyclic core structure, an unusual intramolecular and diastereoselective Nozaki-Hiyama-Kishi reaction involving a ketone as electrophilic coupling partner was developed. In addition, synthetic approaches toward the related natural product (2R)-hydroxy-norneomajucin, featuring a Mn-mediated radical cyclization for the tricycle assembly and a regioselective OH-directed C-H activation are presented.

Enantioselecitve intramolecular C-H insertion of α-diazo β-keto esters catalyzed by homochiral rhodium(II) carboxylates

Enantioselective intramolecular C-H insertion reaction of α-diazo β-keto esters has been achieved by exploiting homochiral rhodium(II) carboxylates, affording optically active cyclopentane derivatives in up to 46% ee.

A SHORT ACCESS TO IRIDOID PRECURSORS

A general approach to C-5 oxygenated iridoids is obtained by photoreductive cyclization of δ,ε-acetylenic cyclopentanones.