Method for the rapid synthesis of highly functionalized 2-hydroxy-1-naphthoates. Syntheses of the naphthoic acid components of neocarzinostatin chromophore and N1999A2

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4551-4553

  Ji, Nan ^a   Rosen, Brad M ^a   Myers, Andrew G ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZALDEHYDE DERIVATIVE; ESTER DERIVATIVE; N 1999A2; NAPHTHOL DERIVATIVE; PHOSPHONIC ACID ESTER; REAGENT; TRIFLUOROETHANOL; UNCLASSIFIED DRUG; ZINOSTATIN;

ALKALINITY; ARTICLE; CHROMATOPHORE; CYCLIZATION; DEGRADATION KINETICS; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; OLEFINATION; OXIDATION KINETICS; QUANTUM YIELD; REACTION ANALYSIS; REPRODUCIBILITY; STRUCTURE ANALYSIS;

EID: 10044266572     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048075l     Document Type: Article

References (23)

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14. Phenyl phosphonate ester 6 was synthesized in two steps from 2,2,6-trimethyl-4H-1,3-dioxane-4-one (see Supporting Information). The corresponding ethyl phosphonate ester is known and has been employed in E-selective olefination reactions: Boeckman, R.; Thomas, A. J. Org. Chem. 1982, 47, 2823-2824.
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18. Manganese(III) acetate was introduced as a reagent for the oxidative cyclization of unsaturated 1,3-dicarbonyl compounds (dihydrofuran products: Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1974, 39, 3456-3457) and has been shown to be useful for the formation of carbocyclic products from unsaturated β-keto acids (Corey, E. J.; Kang, M.-C. J. Am. Chem. Soc. 1984, 106, 5384-5385) and β-keto esters (Snider, B. B.; Mohan, R. M.; Kates, S. A. J. Org. Chem. 1985, 50, 3659-3661). Review: Snider, B. B. Chem. Rev. 1996, 96, 339-363.
19. Manganese(III) acetate was introduced as a reagent for the oxidative cyclization of unsaturated 1,3-dicarbonyl compounds (dihydrofuran products: Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1974, 39, 3456-3457) and has been shown to be useful for the formation of carbocyclic products from unsaturated β-keto acids (Corey, E. J.; Kang, M.-C. J. Am. Chem. Soc. 1984, 106, 5384-5385) and β-keto esters (Snider, B. B.; Mohan, R. M.; Kates, S. A. J. Org. Chem. 1985, 50, 3659-3661). Review: Snider, B. B. Chem. Rev. 1996, 96, 339-363.
20. Manganese(III) acetate was introduced as a reagent for the oxidative cyclization of unsaturated 1,3-dicarbonyl compounds (dihydrofuran products: Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1974, 39, 3456-3457) and has been shown to be useful for the formation of carbocyclic products from unsaturated β-keto acids (Corey, E. J.; Kang, M.-C. J. Am. Chem. Soc. 1984, 106, 5384-5385) and β-keto esters (Snider, B. B.; Mohan, R. M.; Kates, S. A. J. Org. Chem. 1985, 50, 3659-3661). Review: Snider, B. B. Chem. Rev. 1996, 96, 339-363.
21. Manganese(III) acetate was introduced as a reagent for the oxidative cyclization of unsaturated 1,3-dicarbonyl compounds (dihydrofuran products: Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1974, 39, 3456-3457) and has been shown to be useful for the formation of carbocyclic products from unsaturated β-keto acids (Corey, E. J.; Kang, M.-C. J. Am. Chem. Soc. 1984, 106, 5384-5385) and β-keto esters (Snider, B. B.; Mohan, R. M.; Kates, S. A. J. Org. Chem. 1985, 50, 3659-3661). Review: Snider, B. B. Chem. Rev. 1996, 96, 339-363.
22. Aromatic aldehyde used as starting material (9) was prepared in four steps and 51% yield from commercially available 3-methoxybenzyl alcohol (See Supporting Information).
23. 3, HOAc, 40°C, 93% over two steps). Significantly, neither the corresponding E-isomeric β-keto methyl ester (13) nor the saturated β-keto methyl ester (14, cf. Scheme 1) was observed to cyclize under these or other conditions examined.