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Synthesis of flavonoid-type compounds from methyl dehydroabietates

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Abstract

The synthesis of new flavone-type compounds bearing several chiral centres, 12- and 14-(2′-chromonyl)dehydroabietates, are reported. This synthesis started from the aldol condensation of methyl 12- and 14-formyldehydroabietates with 2′-hydroxyacetophenones in order to prepare the corresponding chalcone-type compounds, which were then transformed in the expected flavone-type compounds by cyclodehydrogenation with DMSO and a catalytic amount of iodine. All compounds were exhaustively characterised by NMR and MS techniques.

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References

  • LF Fieser WP Campbell (1938) J Am Chem Soc 60 2631 Occurrence Handle10.1021/ja01278a024 Occurrence Handle1:CAS:528:DyaA1MXktVCk

    Article  CAS  Google Scholar 

  • PF Richtie TF Sanderson LF McBurney (1954) J Am Chem Soc 76 723 Occurrence Handle10.1021/ja01632a026

    Article  Google Scholar 

  • MJ Ohta (1956) Pharm Bull Jpn 4 273 Occurrence Handle1:CAS:528:DyaG2sXks12ksA%3D%3D

    CAS  Google Scholar 

  • B Gigante MJ Marcelo Curto AM Lobo S Prabhakar AJ Slawin HS Rezpa DJ Williams (1989) J Nat Prod 52 85 Occurrence Handle10.1021/np50061a011 Occurrence Handle1:CAS:528:DyaL1MXmtlehtLo%3D

    Article  CAS  Google Scholar 

  • JAS Cavaleiro GMSFC Nascimento MGMS Neves MT Pinto AJD Silvestre MGH Vicente (1996) Tetrahedron Lett 37 1893 Occurrence Handle10.1016/0040-4039(96)00145-1 Occurrence Handle1:CAS:528:DyaK28Xhs1Cmtrg%3D

    Article  CAS  Google Scholar 

  • B Gigante MJ Marcelo Curto AM Lobo S Prabhakar AJ Slawin HS Rezpa DJ Williams (1989) J Nat Prod 52 85 Occurrence Handle10.1021/np50061a011 Occurrence Handle1:CAS:528:DyaL1MXmtlehtLo%3D

    Article  CAS  Google Scholar 

  • RA Franich PD Gagdil (1983) Physiol Plant Pathol 23 183 Occurrence Handle10.1016/0048-4059(83)90001-2 Occurrence Handle1:CAS:528:DyaL2cXjs1Kq

    Article  CAS  Google Scholar 

  • S Savluchinske-Feio L Nunes PT Pereira AM Silva JC Roseiro B Gigante MJM Curto (2007) J Microbiol Methods 70 465 Occurrence Handle10.1016/j.mimet.2007.06.001 Occurrence Handle1:CAS:528:DC%2BD2sXpsFKjsb4%3D

    Article  CAS  Google Scholar 

  • YT Pratt (1951) J Chem Soc C 73 3803 Occurrence Handle1:CAS:528:DyaG38XjvFWjsg%3D%3D

    CAS  Google Scholar 

  • LF Fieser WP Campbell (1939) J Chem Soc C 61 2528 Occurrence Handle1:CAS:528:DyaA1MXlvFyjtA%3D%3D

    CAS  Google Scholar 

  • H Akita T Oishi (1981) Chem Pharm Bull 29 1567 Occurrence Handle1:CAS:528:DyaL3MXlvVOnt7o%3D

    CAS  Google Scholar 

  • H Akita T Oishi (1981) Chem Pharm Bull 29 1580 Occurrence Handle1:CAS:528:DyaL3MXlvVOnt7s%3D

    CAS  Google Scholar 

  • C Moiteiro N Fonseca MJM Curto R Tavares AM Lobo P Ribeiro-Claro V Feliz MGB Drew (2006) Tetrahedron Asymmetry 17 3248 Occurrence Handle10.1016/j.tetasy.2006.11.036 Occurrence Handle1:CAS:528:DC%2BD2sXotFaruw%3D%3D

    Article  CAS  Google Scholar 

  • T Tashima Y Toriumi Y Mochizuki T Nonomura S Nagaoka K Furukawa H Tsuru S Adachi-Akahane T Ohwada (2006) Bioorg Med Chem 14 8014 Occurrence Handle10.1016/j.bmc.2006.07.042 Occurrence Handle1:CAS:528:DC%2BD28XhtFSrtLbL

    Article  CAS  Google Scholar 

  • M Fernandes M Esteves B Gigante N Chattopdhyay (2007) J Fluoresc 7 31

    Google Scholar 

  • BA Bohm (1994) NoChapterTitle JB Harborne (Eds) The Flavonoids – Advances in Research Since 1986 Chapman and Hall London 387

    Google Scholar 

  • DN Dhar (1981) The Chemistry of Chalcones and Related Compounds Wiley New York

    Google Scholar 

  • RJ Anto K Sukumaran G Kuttan MNA Rao V Subbaraju R Kuttan (1995) Cancer Lett 97 33 Occurrence Handle10.1016/0304-3835(95)03945-S Occurrence Handle1:CAS:528:DyaK2MXoslGnsLY%3D

    Article  CAS  Google Scholar 

  • VS Parmar KS Bisht R Jain S Singh KS Sharma S Gupta S Malhotra OD Tyagi A Vardhan HN Pati DV Berghe A Vlietinck (1996) Indian J Chem 35B 220 Occurrence Handle1:CAS:528:DyaK28Xht1SgsLc%3D

    CAS  Google Scholar 

  • CA Calliste JC Le Bail P Trouillas C Pouget G Habrioux AJ Chuliqa JL Duroux (2001) Anticancer Res 21 3949 Occurrence Handle1:CAS:528:DC%2BD38Xis1art7w%3D

    CAS  Google Scholar 

  • A Kumar SB Katiyar A Agarwal PMS Chauhan (2003) Curr Med Chem 10 1137 Occurrence Handle10.2174/0929867033457494 Occurrence Handle1:CAS:528:DC%2BD3sXksFSitLk%3D

    Article  CAS  Google Scholar 

  • ML Go X Wu XL Liu (2005) Curr Med Chem 12 483 Occurrence Handle1:CAS:528:DC%2BD2MXhsFehsLs%3D

    CAS  Google Scholar 

  • Gacche RN, Dhole NA, Kamble SG, Bandgar BP (2007) J. Enz Inhib Med Chem 22, Doi: 10.1080/14756360701306370

  • T Sasayama K Tanaka K Mizukawa A Kawamura T Kondoh K Hosoda E Kohmura (2007) J Neuro-Oncol 85 123 Occurrence Handle10.1007/s11060-007-9395-2 Occurrence Handle1:CAS:528:DC%2BD2sXhtl2gs73M

    Article  CAS  Google Scholar 

  • AJD Silvestre SMCS Monteiro AMS Silva JAS Cavaleiro V Félix P Ferreira MGB Drew (1998) Monatsh Chem 129 1183 Occurrence Handle1:CAS:528:DyaK1cXnvVaiur4%3D

    CAS  Google Scholar 

  • AIRNA Barros AMS Silva I Alkorta J Elguero (2004) Tetrahedron 60 6513 Occurrence Handle10.1016/j.tet.2004.06.005 Occurrence Handle1:CAS:528:DC%2BD2cXmtFKksbk%3D

    Article  CAS  Google Scholar 

  • Brito CM, Pinto DCGA, Silva AMS, Silva AMG, Tomé AC, Cavaleiro JAS (2006) Eur J Org Chem:2558;

  • AIRNA Barros AMS Silva (2006) Magn Reson Chem 44 1122 Occurrence Handle10.1002/mrc.1895 Occurrence Handle1:CAS:528:DC%2BD28Xht12hurbL

    Article  CAS  Google Scholar 

  • DT Patoilo AMS Silva DCGA Pinto AC Tomé JAS Cavaleiro (2007) J Heterocycl Chem 44 1345 Occurrence Handle1:CAS:528:DC%2BD2sXhtlartLzO Occurrence Handle10.1002/jhet.5570440617

    Article  CAS  Google Scholar 

  • Pinto DCGA, Silva AMS, Cavaleiro JAS, Synlett:1897

  • H Meier H Kretzschmann H Kolshorn (1992) J Org Chem 57 6847 Occurrence Handle10.1021/jo00051a033 Occurrence Handle1:CAS:528:DyaK38XmsFWjsbc%3D

    Article  CAS  Google Scholar 

  • AMS Silva DCGA Pinto JAS Cavaleiro (1994) Tetrahedron Lett 35 5899 Occurrence Handle10.1016/S0040-4039(00)78214-1 Occurrence Handle1:CAS:528:DyaK2cXmtlSms7s%3D

    Article  CAS  Google Scholar 

  • L Ramalho B Gigante M Curto F Florêncio (1995) Eur Mass Spectrom 1 389 Occurrence Handle10.1255/ejms.123 Occurrence Handle1:CAS:528:DyaK2MXpvVWisro%3D

    Article  CAS  Google Scholar 

  • TJ Mabry A Ulubelen (1980) NoChapterTitle GR Waller OC Dermer (Eds) Biochemical Application of Mass Spectrometry, 1st supplementary volume John Wiley & Sons New York 1131

    Google Scholar 

  • A Bax (1984) J Magn Reson 57 314 Occurrence Handle1:CAS:528:DyaL2cXhvVCmu7s%3D

    CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Chemistry Department, University of Aveiro, Aveiro, Portugal

    Silvia M. C. S. Monteiro, Armando J. D. Silvestre, Artur M. S. Silva & José A. S. Cavaleiro

Authors
  1. Silvia M. C. S. Monteiro
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  2. Armando J. D. Silvestre
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  3. Artur M. S. Silva
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  4. José A. S. Cavaleiro
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Corresponding author

Correspondence to José A. S. Cavaleiro.

Additional information

Present address: Silvia M. C. S. Monteiro, Environment Department, Polytechnic Institute of Leiria, 2411–901 Leiria, Portugal.

Correspondence: José A. S. Cavaleiro, Chemistry Department, University of Aveiro, 3810-193 Aveiro, Portugal.

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Monteiro, S., Silvestre, A., Silva, A. et al. Synthesis of flavonoid-type compounds from methyl dehydroabietates. Monatsh Chem 139, 1119–1126 (2008). https://doi.org/10.1007/s00706-008-0889-1

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  • DOI: https://doi.org/10.1007/s00706-008-0889-1

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