(-)-Corey lactone benzoate
[CAS# 39746-00-4]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: (-)-Corey lactone benzoate
• Synonyms: (3aR,4S,5R,6aS)-(-)-5-(Benzoyloxy)-hexahydro-4(-hydroxymethyl)-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28
• CAS Registry Number: 39746-00-4
• EC Number: 254-615-6
• SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=CC=C3)CO

Properties

• Melting point: 116-120 °C
• alpha: -80 ° (c=0.8, CHCl3 25 °C)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H332
• Safety Statements: P261-P264-P270-P271-P280-P301+P317-P302+P352-P304+P340-P317-P321-P330-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

(-)-Corey lactone benzoate is a derivative of (-)-Corey lactone, a compound named after E.J. Corey, a pioneering chemist in the field of synthetic organic chemistry. The discovery of (-)-Corey lactone, along with its derivatives like the benzoate ester, has played a significant role in advancing enantioselective synthesis. E.J. Corey’s development of methodologies for stereocontrolled synthesis laid the foundation for the creation of such compounds, which are crucial intermediates in the synthesis of complex organic molecules.

(-)-Corey lactone benzoate is synthesized by reacting (-)-Corey lactone with benzoic acid, typically using coupling agents like dicyclohexylcarbodiimide (DCC) to form the ester bond. This reaction retains the stereochemical integrity of the original lactone, while introducing the benzoate ester group, which provides additional reactivity and functional versatility.

The compound’s utility is primarily in asymmetric synthesis, where the stereocontrol offered by the lactone core is valuable in producing enantiomerically pure compounds. These enantiopure compounds are critical in pharmaceutical chemistry, as the biological activity of many drugs depends on their stereochemistry. (-)-Corey lactone benzoate serves as a chiral building block in the synthesis of complex natural products, prostaglandins, and other bioactive molecules. The benzoate ester moiety also introduces aromatic character, which can influence both the reactivity and physical properties of the resulting compounds.

In addition to its role as an intermediate in complex molecule synthesis, (-)-Corey lactone benzoate has applications in catalysis. Its stereochemically defined structure allows it to be used as a ligand or chiral auxiliary in enantioselective catalytic processes. This makes it a valuable tool in reactions requiring precise stereochemical outcomes, such as the formation of chiral centers in pharmaceuticals and other fine chemicals.

Overall, (-)-Corey lactone benzoate is a key reagent in modern synthetic organic chemistry, with applications in the synthesis of biologically important molecules and in catalysis for producing chiral compounds.

References

2010. Synthesis of ONO-4819. Synfacts.
DOI: 10.1055/s-0029-1219301

2008. Chemo-enzymatic fluorination of unactivated organic compounds. Nature Chemical Biology.
DOI: 10.1038/nchembio.128

2005. One-Pot Versions of the Sulfonate Displacement Route Using Alkane- or Arenesulfonyl Fluorides. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-034-00066