Synthesis of phthalascidin analogs

被引：44
作者：
González, JF [1 ]
Salazar, L [1 ]
de la Cuesta, E [1 ]
Avendaño, C [1 ]
机构：
[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
来源：
TETRAHEDRON | 2005年 / 61卷 / 31期
关键词：
piperazine-2,5-diones; antitumor antibiotics; tetrahydroisoquinolines; N-acyliminium; alpha-amidoalkylation;
D O I：
10.1016/j.tet.2005.05.068
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a new approach to obtain phthalascidin analogs. 6-Phthalimidomethylpyrazino[1,2-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-dehydroisoquino[3,2-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. (c) 2005 Elsevier Ltd. All rights reserved.
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收藏
页码：7447 / 7455
页数：9
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