A simple and efficient method for the preparation of 1-benzyloxy-5- hydroxynaphthalene

Synlett

Volumn , Issue 3, 1999, Pages 330-332

  Becher, Jan ^a   Matthews, Owen A ^a   Nielsen, Mogens B ^a   Raymo, Françisco M ^a   Stoddart, J Fraser ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

1,5 dihydroxynaphthalene; Deprotection; Protection

Indexed keywords

1 BENZYLOXY 5 HYDROXYNAPHTHALENE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ALKYLATION; ARTICLE; COMPLEX FORMATION; DRUG ISOLATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; PROTEIN ASSEMBLY; REACTION ANALYSIS;

EID: 0344061518     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2610     Document Type: Article

References (22)

1. X-ray crystal structure determination (E-mail: mcra@uv.es)
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18. This procedure represents a simple alternative for the generation of tetrabutylammonium enolates of β-dicarbonyl compounds. See, Shono, T.; Kashimura, S.; Sawamura, M.; Soejima, T. J. Org. Chem. 1988, 53, 907.
19. Although the addition of α-ketocarbenoids to olefinic bonds has extensively been used in synthesis, very few examples have been reported of addition to conjugated ketones (see : Davies, H. M. L. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4 (Semmelhach, M. F. Ed.), Chap. 8, p 103). To our knowledge this is the first example that utilizes this reaction for the construction of a natural polycyclic framework. The high yield obtained in the cyclopropanation reaction of 8 contrasts with the poor results obtained in the few examples of this reaction described so far (see: Burke, S. D.; Grieco, P. A. Organic Reactions, Vol. 26, Chap. 2; Dauben, W. G., Ed; John Wiley & Sons: New York, 1979; p 361). It is unknown if the cyclopropanation reaction occurs via a ketocarbenoid intermediate, an unfavourable process due to the electrophilic character of this species and the adverse electron-withdrawing effect of the carbonyl group on the reactivity of the double bond, or by dipolar cycloaddition of the diazocarbonyl moiety to the α,β-unsaturated system followed by dinitrogen extrusion (see: Doyle, M. P.; Dorow, R. L.; Tamblyn, W. H. J. Org. Chem. 1982, 47, 4059). In any case, control experiments showed that the reaction (conversion of 8 into 16) also takes place in the absence of the copper catalyst but at 190 °C in toluene and in no useful synthetic yield.
20. -3.
21. It should be mentioned that no hydrogenolysis of the other cyclopropane ring was observed, even under more forcing hydrogenation conditions.
22. +) calcd 304.2402, obsd 304.2399.