Total synthesis of ecteinascidin 743

被引：157

作者：

Chen, JC ^{[1
]}

Chen, XC ^{[1
]}

Bois-Choussy, M ^{[1
]}

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 01期

关键词：

D O I：

10.1021/ja0571794

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent total synthesis of ecteinascidin 743 is realized from five building blocks of almost equal size. It takes 23 steps from l-3-hydroxy-4-methoxy-5-methyl phenylalanol (5) with an overall yield of 3%. Copyright © 2006 American Chemical Society.

引用

页码：87 / 89

页数：3

共 43 条

[1] DIASTEREOSELECTIVITY AND ENANTIOSELECTIVITY IN THE PICTET-SPENGLER REACTION [J].

BAILEY, PD ;

HOLLINSHEAD, SP ;

MCLAY, NR ;

MORGAN, K ;

PALMER, SJ ;

PRINCE, SN ;

REYNOLDS, CD ;

WOOD, SD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04) :431-439

[2] SYNTHESIS OF ISOQUINOLINES .3. A NEW SYNTHESIS OF 1,2,3,4-TETRAHYDROISOQUINOLINES [J].

BOBBITT, JM ;

KIELY, JMN ;

KHANNA, KL ;

EBERMANN, R .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (07) :2247-+

[3] Synthetic studies toward ecteinascidin 743 [J].

Chen, XC ;

Chen, JC ;

De Paolis, M ;

Zhu, JP .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4397-4408

[4] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[5] Synthesis of ecteinascidin ET-743 and phthalascidin Pt-650 from cyanosafracin B [J].

Cuevas, C ;

Pérez, M ;

Martín, MJ ;

Chicharro, JL ;

Fernández-Rivas, C ;

Flores, M ;

Francesch, A ;

Gallego, P ;

Zarzuelo, M ;

de la Calle, F ;

García, J ;

Polanco, C ;

Rodríguez, I ;

Manzanares, I .

ORGANIC LETTERS, 2000, 2 (16) :2545-2548

[6] A short enantioselective synthesis of protected L-3-hydroxy-4-methoxy-5-methyl phenylalanine and its corresponding aldehyde - A common subunit of ecteinascidin-743, safracin and congeners [J].

De Paolis, M ;

Chen, XC ;

Zhu, JP .

SYNLETT, 2004, (04) :729-731

[7] Synthetic studies on ecteinascidin 743: rapid access to the fully functionalized tetrahydroisoquinoline with a bridged 10-membered sulfur containing macrocycle [J].

De Paolis, M ;

Chiaroni, A ;

Zhu, JP .

CHEMICAL COMMUNICATIONS, 2003, (23) :2896-2897

[8] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[9] A PERIODONIUM TRIFLUOROMETHANESULFONATE - AN ISOLABLE 10-1-4 ORGANOIODINE SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (03) :902-903

[10] Total synthesis of ecteinascidin 743 [J].

Endo, A ;

Yanagisawa, A ;

Abe, M ;

Tohma, S ;

Kan, T ;

Fukuyama, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6552-6554

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