Synthesis of topostins B567 and D654 (WB-3559D, flavolipin), DNA topoisomerase I inhibitors of bacterial origin

被引：16

作者：

Shioiri, T ^{[1
]}

Terao, Y ^{[1
]}

Irako, N ^{[1
]}

Aoyama, T ^{[1
]}

机构：

[1] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 51期

关键词：

topostin; enzyme inhibitors; asymmetric reaction; coupling;

D O I：

10.1016/S0040-4020(98)00984-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Topostins B567 (2b) and D654 (3b) (WB-3559D, flavolipin) have been efficiently synthesized from 1,10-decanediol (5) in 11 and 13 steps, respectively, involving an asymmetric hydrogenation of the beta-keto ester 14 using (R)-BINAP ruthenium bromide and a peptide coupling using diethyl phosphorocyanidate (DEPC, (EtO)(2)P(O)CN) as key steps. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：15701 / 15710

页数：10

共 19 条

[1]

Ando, COMMUNICATION

[2] C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS [J].

BROOKS, DW ;

LU, LDL ;

MASAMUNE, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :72-74

[3] Total synthesis of analogs of topostin B, a DNA topoisomerase I inhibitor. Part 4. Synthesis of topostin B-2 analogs [J].

Fujiwara, H ;

Egawa, S ;

Terao, Y ;

Aoyama, T ;

Shioiri, T .

TETRAHEDRON, 1998, 54 (3-4) :565-572

[4] Total synthesis of analogs of topostin B, a DNA topoisomerase I inhibitor. Part 3. Improved synthesis of topostin B-1 analogs [J].

Fujiwara, H ;

Aoyama, T ;

Shioiri, T .

TETRAHEDRON, 1998, 54 (3-4) :551-564

[5]

GENET JP, 1995, TETRAHEDRON LETT, V36, P4801

[6]

GREZESZCZYK B, 1992, POLISH J CHEM, V66, P1627

[7] Total synthesis of sulfobacin A (Flavocristamide B) [J].

Irako, N ;

Shioiri, T .

TETRAHEDRON LETTERS, 1998, 39 (32) :5793-5796

[8] Synthesis of sulfobacin B [J].

Irako, N ;

Shioiri, T .

TETRAHEDRON LETTERS, 1998, 39 (32) :5797-5798

[9] SULFOBACIN-A AND SULFOBACIN-B, NOVEL VON-WILLEBRAND-FACTOR RECEPTOR ANTAGONISTS .2. STRUCTURAL ELUCIDATION [J].

KAMIYAMA, T ;

UMINO, T ;

ITEZONO, Y ;

NAKAMURA, Y ;

SATOH, T ;

YOKOSE, K .

JOURNAL OF ANTIBIOTICS, 1995, 48 (09) :929-936

[10] PHOSPHOLIPIDS AND A NOVEL GLYCINE-CONTAINING LIPOAMINO ACID IN CYTOPHAGA-JOHNSONAE STANIER STRAIN C21 [J].

KAWAZOE, R ;

OKUYAMA, H ;

REICHARDT, W ;

SASAKI, S .

JOURNAL OF BACTERIOLOGY, 1991, 173 (17) :5470-5475

← 1 2 →