Synthesis of precursors for the oxidative tandem cyclization of diphenolsto galanthamine analogs

Molecules

Volumn 7, Issue 1, 2002, Pages 18-25

  Treu, Matthias ^a   Jordis, Ulrich ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Deoxygenation of benzyl alcohols; Isopropyl ether protecting group; O dealkylation; Tandem cyclization

Indexed keywords

4 BROMO 5 [2 (4 HYDROXYBENZYL)BENZYL] 2 METHOXYPHENOL; 4 BROMO 5 [4 (4 HYDROXYPHENYL)BUTYL] 2 METHOXYPHENOL; GALANTAMINE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; OXIDATION; PRECURSOR; REACTION ANALYSIS;

EID: 3543006546     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/70100018     Document Type: Article

References (16)

1. Node, M.; Kodama, S.; Hamashima, Y.; Baba, T.; Hamamichi, N.; Nishide, K. An efficient synthesis of (±)-narwedine and (±)-galanthamine by an improved phenolic oxidative coupling. Angew. Chem., Int. Ed., 2001, 40, 3060-3062.
2. Giacobini, E. Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications. Neurochem. Int. 1998, 32, 413-419.
3. Arisawa, M.; Tohma, H.; Kita, Y. Development of intramolecular oxidative phenolic coupling reactions using hypervalent iodine (III) reagents and their application to the synthesis of Amaryllidaceae alkaloids. Yakugaki Zasshi, J. Pharm. Soc. Japan 2000, 120, 1061-1073.
4. Franck, B.; Dunkelmann, G.; Lubs, H. J. Alkaloid syntheses by oxidative condensation under biogenetic conditions. IX. Synthesis of a morphinan derivative by oxidative ring closure. Angew. Chem., Int. Ed. Engl. 1967, 6, 1075-1076.
5. Schwartz, M. A.; Holton, R. A. Intramolecular oxidative phenol coupling. II. Biogenetic-type synthesis of (±)-maritidine. J. Amer. Chem. Soc. 1970, 92, 1090-1092.
6. Kametani, T.; Yamaki, K.; Yagi, H.; Fukumoto, K. Studies on the syntheses of heterocyclic compounds. CCCXV. Modified total synthesis of (-)-galanthamine through phenol oxidation. J. Chem. Soc. C 1969, 2602-2605.
7. Barton, D. H. R.; Kirby, G. W. Phenol oxidation and biosynthesis. V. Synthesis of galanthamine. J. Chem. Soc. 1962, 806-817.
8. Kametani, T.; Seino, C.; Yamaki, K.; Shibuya, S.; Fukumoto, K.; Kigasawa, K.; Satoh, F.; Hiiragi, M.; Hayasaka, T. Syntheses of heterocyclic compounds. CCCLXXXVI. Alternative total syntheses of galanthamine and N-benzylgalanthamine iodide. J. Chem. Soc. C 1971, 1043-1047.
9. (a) 1,3-Dihydrospiro(isobenzofuran)ene. NL 7416115, 1975 [Chem. Abstr.: 84:164641].
10. (b) Heidenreich, J. Ueber Indoxazene. Chem. Ber. 1894, 27, 1452-1456.
11. Munakata, K.; Tanaka, S.; Toyoshima, S. Therapy for urolithiasis with hydroxamic acids. I. Synthesis of new N-(aroyl)glycinohydroxamic acid derivatives and related compounds. Chem. Pharm. Bull. 1980, 28, 2045-2051.
12. Martin, L. L.; Klioze, S. S.; Worm, M.; Crichlow, C. A.; Geyer, H. M., III; Kruse, H. Synthesis of spiro[isobenzofuran-1(3H),4′-piperidines] as potential central nervous system agents. 5. Conformationally mobile analogs derived by furan ring opening. J. Med. Chem. 1979, 22, 1347-1354.
13. 14. J. Org. Chem. 1953, 18, 489-492.
14. Treu, M.; Jordis, U.; Mereiter, K. 12H-[2]-Benzothiepino[6,5a,5-bc] benzofuran: Synthesis of a Sulfur-Analog of Galanthamine. Heterocycles, 2001, 55, 1727-1735.
15. Lau, C. K.; Tardif, S.; Dufresne, C.; Scheigetz, J. Reductive deoxygenation of aryl aldehydes and ketones by tert-butylamine-borane and aluminum chloride. J. Org. Chem. 1989, 54, 491-494.
16. Unpublished results