Preparation of 5-Deoxypterocarpens by a-Arylation of Tetralones with o-Bromo-methoxyarenes Followed by BBr3 Mediated Cyclization

Preparation of 5-Deoxypterocarpens by a-Arylation of Tetralones with o-Bromo-methoxyarenes Followed by BBr3 Mediated Cyclization

Fernandes, Talita de A.; Domingos, Jorge L. O.; Rocha, Luiza I. A. da; Medeiros, Sabrina de; Nájera, Carmen; Costa, Paulo R. R.

Abstract:

Pterocarpens are members of the family of isoflavonoids, natural products that are produced in response to microbial infections. It was reported that pterocarpens (1) and 5-deoxyanalogues (2), bind to estrogenic receptors (ERs) as strong as the natural ligand 17-estradiol (Fig. 1). These compounds were claimed to be useful for the treatment of cancer and other hormone-dependent diseases. Some strategies for the preparation of deoxypterocarpens are described in literature, but they are labourious and low yielding.We envisaged that the most straightforward and green approach to prepare these compounds would be the direct -arylation of tetralones with o-halogen O-protected phenols, followed by desprotection and cyclization.

Pterocarpens are members of the family of isoflavonoids, natural products that are produced in response to microbial infections. It was reported that pterocarpens (1) and 5-deoxyanalogues (2), bind to estrogenic receptors (ERs) as strong as the natural ligand 17-estradiol (Fig. 1). These compounds were claimed to be useful for the treatment of cancer and other hormone-dependent diseases. Some strategies for the preparation of deoxypterocarpens are described in literature, but they are labourious and low yielding.We envisaged that the most straightforward and green approach to prepare these compounds would be the direct -arylation of tetralones with o-halogen O-protected phenols, followed by desprotection and cyclization.

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DOI: 10.5151/chempro-15bmos-BMOS2013_20131014133355

Referências bibliográficas

• [1] 1 Miller, C. P. et al. U.S. Pat. Appl. Publ. (2006), US 2006/0004087
• [2] 2 F. Bellina, T. Masini, R. Rossi, Eur. J. Org. Chem. 2010, 1339-44

Como citar:

Fernandes, Talita de A.; Domingos, Jorge L. O.; Rocha, Luiza I. A. da; Medeiros, Sabrina de; Nájera, Carmen; Costa, Paulo R. R.; "Preparation of 5-Deoxypterocarpens by a-Arylation of Tetralones with o-Bromo-methoxyarenes Followed by BBr3 Mediated Cyclization", p-301-301. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_20131014133355