Model studies on the synthesis of the natural meroterpenoid cordiaquinone A
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Keywords

Meroterpenoid naphthoquinone
Cordia corymbosa
Boraginaceae
ε-caprolactone
Epoxycitronellol
Organocuprate

How to Cite

Batalini, C., & Bieber, L. W. (2001). Model studies on the synthesis of the natural meroterpenoid cordiaquinone A. Eclética Química, 26(1), 69–76. https://doi.org/10.26850/1678-4618eqj.v26.1.2001.p69-76

Abstract

Two main strategies for the synthesis of the natural meroterpenoid cordiaquinone A (1) - isolated of the roots of Cordia corymbosa G. Don (Boraginaceae) - were tested on model compounds. Whereas all attempts of alkylation of e-caprolactone (10) were unsuccessful, the coupling of epoxycitronellol (17) with an appropriate organocuprate proceeded in the expected direction.

https://doi.org/10.26850/1678-4618eqj.v26.1.2001.p69-76
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References

BENTLEY, M.D.; DEWAR, M.J.S. The Solvolysis of 2-Arylethyl-p-Toluenesulfonates. J. Am. Chem. Soc., v.92, p.3996-4002, 1970. [ Links ]

BIEBER, L.W. et al. Meroterpenoid Naphthoquinones From Cordia corymbosa. Phytochemistry, v.29, n.6, p.1955-1959, 1990. [ Links ]

BIEBER, L.W. et al. Further Meroterpenoid Naphthoquinones from Cordia corymbosa. Phytochemistry, v.35, p.1027-1028, 1994. [ Links ]

GRIECO, P.A.; HIROI, K. Model Studies Directed Toward the Total Synthesis of Vernolepin: Construction of the a-Methylene-d-Lactone Portion of Vernolepin. Tetrahedron Letters, n.21, p.1831-1834, 1973. [ Links ]

KARRER, P. et al. Synthese des 2-phytyl-naphtochinons-1,4. Helv. Chim. Acta, v.23, p.585-590, 1940. [ Links ]

KOETZ, A.; STECHE, T. Über die Stufenweise Oxydation des Citronellols und Geraniols. J. Prakt. Chem., v.107, p.193-210, 1924. [ Links ]

OLAH, G.A.; SINGH, B.P. Stable Carbocations. a-Ethylenenaphthalenium Ions. J. Am. Chem. Soc., v.104, n.19, p.5168-5172, 1982. [ Links ]

OVERBERGER, C.G.; KAYE, H. The Syntheses of Some Optically Active e-Caprolactones. J. Am. Chem. Soc., v.89, n.22, p.5640-5646, 1967. [ Links ]

PATERSON, I.; FLEMING, I. a-Methylenation of lactones and Esters Zinc Bromide-Catalysed Phenylthiomethylation of o-Silylated Enolates. Tetrahedron Letters, n.11, p.993-994, 1979. [ Links ]

POSNER, G.H. Substitution reactions using organocopper reagents. Organic Reaction, v.22, p.253-400, 1975. [ Links ]

REETZ, M.T. Lewis acid induced alfa-alkylation of carbonyl compounds. Angew. Chem. Int. Ed. Engl., v.21, p.96-108, 1982. [ Links ]

SKARZEWSKI, J. Cerium Catalyzed Persulfate Oxydation of Polycyclic Aromatic Hydrocarbons to Quinones. Tetrahedron, v.40, n.23, p.4997-5000, 1984. [ Links ]

THOMAS, A.F.; REY, F. The Baeyer-Villiger Reaction of Pinanones (Bicyclo[3.1.1]heptanones). Tetrahedron, v.48, n.10, p.1927-1942, 1992. [ Links ]

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