Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions

被引：50

作者：

Chandrasekhar, S. ^{[1
]}

Reddy, N. Ramakrishna ^{[1
]}

Rao, Y. Srinivasa ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Nat Prod Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 51期

关键词：

ecteinascidin-743; tetrahydroisoquinolines; Heck reaction; aza-Michael reaction; Baeyer-Villiger reaction; ANTI-TUMOR ANTIBIOTICS; ABC RING MODEL; ENANTIOSELECTIVE SYNTHESIS; PRACTICAL SYNTHESIS; CARIBBEAN TUNICATE; NATURAL-PRODUCT; AMINO-ACID; EFFICIENT; DRUG; CONSTRUCTION;

D O I：

10.1016/j.tet.2006.09.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：12098 / 12107

页数：10

共 6 条

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