Synthesis of phthalascidin analogs |
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Authors: | J Francisco González |
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Institution: | Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia. Universidad Complutense, 28040 Madrid, Spain |
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Abstract: | We report a new approach to obtain phthalascidin analogs. 6-Phthalimidomethylpyrazino1,2-b]isoquinoline-1,4-dione (5a) was obtained in a one-pot N-alkylation/cyclization of the corresponding 1-acetyl-3-arylmethyl-2,5-piperazinedione with N-phthalylacetaldehyde dimethyl acetal. Chemoselective reduction of the C(1)-carbonyl group in the 3-arylmethyl-11,11a-dehydroderivative 9a was followed by cyclization of an acyliminium intermediate, to give the 6,15-imino-7-oxo-14,14a-dehydroisoquino3,2-b]3-benzazocin 11a. Alternatively, the octacyclic compound 13a was obtained through a novel double cyclization of a precursor in which the C(1)-carbonyl and one phthalimide carbonyl group were reduced. |
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Keywords: | Piperazine-2 5-diones Antitumor antibiotics Tetrahydroisoquinolines N-Acyliminium α-Amidoalkylation |
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