Stereocontrolled total synthesis of (-)-ephedradine A (orantine)

被引：164

作者：

Kurosawa, W ^{[1
]}

Kan, T ^{[1
]}

Fukuyama, T ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 27期

关键词：

D O I：

10.1021/ja036011k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereocontrolled total synthesis of (-)-ephedradine A has been accomplished. The synthesis features an asymmetric C-H insertion reaction, an intramolecular ester-amide exchange reaction, and a Sharpless asymmetric aminohydroxylation reaction. Construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction. Copyright © 2003 American Chemical Society.

引用

页码：8112 / 8113

页数：2

共 23 条

[11] Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A [J].

Kan, T ;

Fujiwara, A ;

Kobayashi, H ;

Fukuyama, T .

TETRAHEDRON, 2002, 58 (32) :6267-6276

[12]

Kan T, 2002, SYNLETT, P697

[13] Highly versatile synthesis of nitrogen-containing compounds by means of nitrobenzenesulfonamides [J].

Kan, T ;

Fukuyama, T .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2001, 59 (08) :779-789

[14]

Kurosawa W, 2003, SYNLETT, P1028

[15]

Kurosawa W., 2002, ORG SYNTH, V79, P186

[16] N-halocarbamate salts lead to more efficient catalytic asymmetric aminohydroxylation [J].

Li, GG ;

Angert, HH ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2813-2817

[17]

Lipton M. F., 1979, Org. Synth., V59, P49, DOI DOI 10.15227/ORGSYN.059.0049

[18] A CONVENIENT PROCEDURE FOR THE MONOSILYLATION OF SYMMETRICAL 1,N-DIOLS [J].

MCDOUGAL, PG ;

RICO, JG ;

OH, YI ;

CONDON, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3388-3390

[19] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[20] Efficient method for preparation of N-methoxy-N-methyl amides by reaction of lactones or esters with Me(2)AlCl-MeONHMe center dot HCl [J].

Shimizu, T ;

Osako, K ;

Nakata, T .

TETRAHEDRON LETTERS, 1997, 38 (15) :2685-2688

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