《General Access to Concave-Substituted cis-Dioxabicyclo[3.3.0]octanones: Enantioselective Total Syntheses of Macfarlandin C and Dendrillolide A》 was written by Allred, Tyler K.; Dieskau, Andre P.; Zhao, Peng; Lackner, Gregory L.; Overman, Larry E.. Electric Literature of C3H3ClO3 And the article was included in Journal of Organic Chemistry in 2020. The article conveys some information:
The evolution of a strategy to access the family of rearranged spongian diterpenoids harboring a concave-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-one fragment is described. The approach involves late-stage fragment coupling of a tertiary-carbon radical and an electron-deficient double bond to form vicinal quaternary and tertiary stereocenters with high fidelity. A stereoselective Mukaiyama hydration is the key step in the subsequent elaboration of the cis-2,8-dioxabicyclo[3.3.0]octan-3-one moiety. This strategy was utilized in enantioselective total syntheses of (-)-macfarlandin C and (+)-dendrillolide A. An efficient construction of enantiopure tetramethyloctahydronaphthalenes was developed during the construction of (-)-macfarlandin C. In addition to this study using Methyl 2-chloro-2-oxoacetate, there are many other studies that have used Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Electric Literature of C3H3ClO3) was used in this study.
Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1.Electric Literature of C3H3ClO3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics