Methods of Synthesizing Corticiolic Acid
AssigneeAmrita Vishwa Vidyapeetham
InventorsNanjan Pandurangan, Sunil Kumar Deevi, Prasanna Ramani
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Abstract
The present invention discloses a method of synthesizing corticiolic acid. More particularly, cost-effective, and efficient methods for synthesizing corticiolic acid using different synthetic methodologies. Each method involves unique reaction conditions and steps, resulting in varying yields. All the methods avoid the use of hazardous pyrophoricreagents and BBr3 for deprotection. The invention provides an eco-friendly process for the synthesis of corticiolic acid and its derivatives.
Claims11
A method for synthesizing corticiolic acid, wherein said method of synthesis comprises the steps of
- a) reacting a compound of formula 1 with phosphorus oxychloride (POCh) and dimethylformamide (DMF) to obtain a compound of formula 2;
- b) reacting the compound of formula 2 with sodium chlorite (NaClO2), sodium dihydrogen phosphate (NalhPO4), and dimethyl sulfoxide (DMSO) in water at a temperature of O° C. to room temperature to obtain a compound of formula 3;
- c) reacting the compound of formula 3 with potassium carbonate (KiCO3), methyl iodide (Cffil), and DMF at a temperature of 50° C. to obtain a compound of formula 4;
- d) reacting the compound of formula 4 with compound of formula 5 in tetrahydrofuran (THF) at a temperature of 50° C. to obtain a compound of formula 6;
- and
- e) reacting the compound of formula 6 with boron tribromide (BBn) to obtain corticiolic acid (compound of formula 7).
A method for synthesizing corticiolic acid, comprising the steps of:
- a) reacting a compound of formula 1 with pentadec-1-ene and 9-borabicyclononane (9-BBN) in tetrahydrofuran (THF) at a temperature of 50° C., followed by reacting the resulting intermediate with potassium carbonate (KiCO3), palladium(II) dichloride (Pd(dppf)Ch) in dichloromethane (DCM), and dimethylformamide (DMF) in water at a temperature of 100° C. to obtain a compound of formula 2;
- b) reacting the compound of formula 2 with phosphorus oxychloride(POCb) and dimethylformamide (DMF) to obtain a compound of formula 3;
- c) reacting the compound of formula 3 with sodium chlorite (NaClOz), sodium dihydrogen phosphate (NaHzPO4), and dimethyl sulfoxide (DMSO) in water at a temperature of O° C. to room temperature to obtain a compound of formula 4;
- and
- d) reacting the compound of formula (IV) with boron tribromide (BBr3) in dichloromethane(DCM) at a temperature of −78° C. to room temperature to obtain corticiolic acid (compound of formula 7.
A method for synthesis of corticiolic acid, wherein said method comprising the steps of:
- a) reacting a compound of formula 1 with pentadec-1-ene, 9-borabicyclononane(9-BBN), and tetrahydrofuran(THF) at a temperature of 50° C., followed by reacting the resulting intermediate with potassium carbonate (K2CO3), palladium(II)dichloride (Pd(dppf)Clz) in dichloromethane (DCM), and dimethylformamide(DMF) in water at a temperature of 100° C. to obtain a compound of formula 2;
- b) reacting the compound of formula 2 with phosphorus oxychloride(POCb) and dimethylformamide (DMF) to obtain a compound of formula 3;
- c) reacting the compound of formula 3 with sodium chlorite (NaClOz), sodium dihydrogen phosphate (NaHzPO4), and dimethyl sulfoxide (DMSO) in water at a temperature of O° C. to room temperature to obtain a compound of formula 4;
- and
- d)reacting the compound of formula 4with a reducing agent to obtain corticiolic acid (compound of formula 7).
Dependencies are inferred from the claim text.