Total synthesis of the marine natural product (-)-cribrostatin 4 (renieramycin H)

被引：55

作者：

Chen, Xiaochuan ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 21期

关键词：

alkaloids; antitumor agents; asymmetric synthesis; domino reactions; marine natural products;

D O I：

10.1002/anie.200700539

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Winning at dominoes: The cytotoxic title compound was synthesized from five readily available starting materials in a longest linear sequence of 21 steps and 4.3% overall yield. The key step in the construction of the pentacyclic core of 1 was a domino sequence involving β elimination and an intramolecular phenolic Mannich reaction. Alloc = allyloxycarbonyl, Bn = benzyl, Boc = tert-butoxycarbonyl. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3962 / 3965

页数：4

共 48 条

[1] Ecteinascidin 743: a novel anticancer drug with a unique mechanism of action [J].

Aune, GJ ;

Furuta, T ;

Pommier, Y .

ANTI-CANCER DRUGS, 2002, 13 (06) :545-555

[2] 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

[3] SYNTHESIS OF 1-(2-HYDROXYARYL)-1,2,3-PROPANETRIOL AND 1-(2-HYDROXYARYL)-2-AMINO-1,3-PROPANEDIOL DERIVATIVES OF EITHER THREO OR ERYTHRO CONFIGURATION [J].

CASIRAGHI, G ;

CORNIA, M ;

RASSU, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4919-4922

[4] The solution to a deep stereochemical conundrum: Studies toward the tetrahydroisoquinoline alkaloids [J].

Chan, C ;

Zheng, SP ;

Zhou, BS ;

Guo, J ;

Heid, RM ;

Wright, BJD ;

Danishefsky, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) :1749-1754

[5] Total synthesis of cribrostatin IV: Fine-tuning the character of an amide bond by remote control [J].

Chan, C ;

Heid, R ;

Zheng, SP ;

Guo, JS ;

Zhou, BS ;

Furuuchi, T ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4596-4598

[6]

CHAN C, 2006, ANGEW CHEM, V118, P1781

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

Chen, JC ;

Chen, XC ;

Bois-Choussy, M ;

Zhu, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :87-89

[8] Asymmetric total syntheses of Ecteinascidin 597 and Ecteinascidin 583 [J].

Chen, Jinchun ;

Chen, Xiaochuan ;

Willot, Matthieu ;

Zhu, Jieping .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) :8028-8032

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

Chen, XC ;

Chen, JC ;

De Paolis, M ;

Zhu, JP .

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

[10] Enantioselective total synthesis of ecteinascidin 743 [J].

Corey, EJ ;

Gin, DY ;

Kania, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (38) :9202-9203

← 1 2 3 4 5 →