A concise route to 3-hydroxy-4-methoxy-5-methylbenzaldehyde derivative

Synthetic Communications

Volumn 30, Issue 13, 2000, Pages 2407-2421

  Saito, Naoki ^a   Tachi, Masashi ^a   Seki, Ryu Ichi ^a   Sugawara, Yayoi ^a   Takeuchi, Eri ^a   Kubo, Akinori ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 4 METHOXY 5 METHYLBENZALDEHYDE DERIVATIVE; ISOQUINOLINE DERIVATIVE; NATURAL PRODUCT; PHENOL DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034033759     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910008086883     Document Type: Article

References (17)

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12. 1H-NMR spectrum of 13, while this NOE was negligible in the spectrum of 7.
13. Direct bromination of 2,3-dimethoxytoluene using NBS in carbon tetrachloride or acetonitrile affording 6-bromo-2,3-dimethoxytoluene in high yield has been reported (see: Gruter, G. -J. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473; Albrecht, M. Synthesis 1996, 230; Knölker, H. -J. and Fröhner W. Tetrahedron Lett. 1997, 38, 1535) . However, the direct conversion of 7 to 10a under similar conditions was unsuccessful, and an inseparable mixture of 10a and 10b was obtained.
14. Direct bromination of 2,3-dimethoxytoluene using NBS in carbon tetrachloride or acetonitrile affording 6-bromo-2,3-dimethoxytoluene in high yield has been reported (see: Gruter, G. -J. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473; Albrecht, M. Synthesis 1996, 230; Knölker, H. -J. and Fröhner W. Tetrahedron Lett. 1997, 38, 1535) . However, the direct conversion of 7 to 10a under similar conditions was unsuccessful, and an inseparable mixture of 10a and 10b was obtained.
15. Direct bromination of 2,3-dimethoxytoluene using NBS in carbon tetrachloride or acetonitrile affording 6-bromo-2,3-dimethoxytoluene in high yield has been reported (see: Gruter, G. -J. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473; Albrecht, M. Synthesis 1996, 230; Knölker, H. -J. and Fröhner W. Tetrahedron Lett. 1997, 38, 1535) . However, the direct conversion of 7 to 10a under similar conditions was unsuccessful, and an inseparable mixture of 10a and 10b was obtained.
16. Banwell, M. G.; Flynn, B. L. and Stewart, S. G. J. Org. Chem. 1998, 63, 9139.
17. Since we completed this paper, selective protection of 2,3-dihydroxytoluene (4) by TsCl was reported by Fukuyama in his synthetic study on ecteinascidin: Endo, A.; Kann, T. and Fukuyama, T. Synlett. 1999, 1103.