Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-A

被引：43

作者：

Kan, T ^{[1
]}

Fujiwara, A ^{[1
]}

Kobayashi, H ^{[1
]}

Fukuyama, T ^{[1
]}

机构：

[1] Univ Tokyo, Japan Sci & Technol Corp, Grad Sch Pharmaceut Sci, JST,Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 32期

关键词：

lipogrammistin-A; cyclization; Mitsunobu conditions;

D O I：

10.1016/S0040-4020(02)00626-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of medium- and large-sized cyclic amines using alkylation with 2-nitrobenzenesulfonamides is described. Using either conventional alkylation procedures or Mitsunobu conditions, the cyclization reaction proceeded in a highly efficient manner. The usefulness of this methodology has been fully demonstrated in the total synthesis of lipogrammistin-A (9), an 18-membered cyclic polyamine. (C) 2002 Published by Elsevier Science Ltd.

引用

收藏

页码：6267 / 6276

页数：10

相关论文

共 34 条

[1] A direct route to medium and large cyclic amines from aminoalkenes [J].

Bergmann, DJ ;

Campi, EM ;

Jackson, WR ;

Patti, AF ;

Saylik, D .

TETRAHEDRON LETTERS, 1999, 40 (30) :5597-5600

[2] Partial reduction of annulated heterocycles as a general route to medium rings containing oxygen and nitrogen [J].

Donohoe, TJ ;

Raoof, A ;

Linney, IA ;

Helliwell, M .

ORGANIC LETTERS, 2001, 3 (06) :861-864

[3]

FATIMA I, 2001, ORG LETT, V3, P2957

[4]

Fujiwara A, 2000, SYNLETT, P1667

[5]

Fujiwara T, 2000, HETEROCYCLES, V52, P147

[6]

Fukuyama T, 1999, SYNLETT, P1301

[7] 2,4-dinitrobenzenesulfonamides: A simple and practical method for the preparation of a variety of secondary amines and diamines. [J].

Fukuyama, T ;

Cheung, M ;

Jow, CK ;

Hidai, Y ;

Kan, T .

TETRAHEDRON LETTERS, 1997, 38 (33) :5831-5834

[8] FACILE REDUCTION OF ETHYL THIOL ESTERS TO ALDEHYDES - APPLICATION TO A TOTAL SYNTHESIS OF (+)-NEOTHRAMYCIN-A METHYL-ETHER [J].

FUKUYAMA, T ;

LIN, SC ;

LI, LP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7050-7051

[9] 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES [J].

FUKUYAMA, T ;

JOW, CK ;

CHEUNG, M .

TETRAHEDRON LETTERS, 1995, 36 (36) :6373-6374

[10] Ring-closing alkyne metathesis.: Stereoselective synthesis of the cytotoxic marine alkaloid motuporamine C [J].

Fürstner, A ;

Rumbo, A .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2608-2611

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