A mild and convenient procedure for the conversion of toxic beta-asarone into rare phenylpropanoids: 2,4,5-trimethoxycinnamaldehyde and gamma-asarone.
Oxidation of beta-asarone (2) with DDQ gave trans-2,4,5-trimethoxycinnamaldehyde (3), which on treatment with p-toluenesulfonyl hydrazine provided corresponding alpha,beta-unsaturated hydrazone derivative (4). Reduction of 4 with sodium borohydride in acetic acid afforded gamma-asarone (1) in 43% yield.
Sinha
Arun K
AK
Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Palampur -176061, India. aksinha8@rediffmail.com
Acharya
Ruchi
R
Joshi
Bhupendra P
BP
D029023:Acorus / Q000737:chemistry*; D000171:Acrolein / Q000031:analogs & derivatives / Q000737:chemistry*; D000081248:Allylbenzene Derivatives; D000840:Anisoles / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002855:Chromatography, Thin Layer; D006835:Hydrazones / Q000737:chemistry*; D007194:India; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry*; D027343:Rhizome / Q000737:chemistry; D013237:Stereoisomerism; D014118:Toxins, Biological / Q000737:chemistry
C461723:2,4,5-trimethoxycinnamaldehyde; C461724:2,4,5-trimethoxycinnamyltosylhydrazone; D000081248:Allylbenzene Derivatives; D000840:Anisoles; D006835:Hydrazones; D014118:Toxins, Biological; C012195:asarone; D000171:Acrolein