Total synthesis of (±)-FR66979

被引：49

作者：

Ducray, R

Ciufolini, MA ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5078, Lab Synthese & Methodol Organ, F-69622 Villeurbanne, France

[2] Ecole Super Chim Phys Elect Lyon, F-69622 Villeurbanne, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2002年 / 41卷 / 24期

关键词：

antitumor agents; asymmetric synthesis; natural products; rearrangement; total synthesis;

D O I：

10.1002/anie.200290017

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unusual fragmentation of aziridine 1, triggered by a preliminary homo-Brook transposition is the key step in the total synthesis of the racemate of the antitumor agent FR66979 (2).

引用

页码：4688 / 4691

页数：4

共 57 条

[11] COVALENT STRUCTURE OF THE DNA-DNA INTERSTRAND CROSS-LINK FORMED BY REDUCTIVELY ACTIVATED FR66979 IN SYNTHETIC DNA DUPLEXES [J].

HUANG, HF ;

PRATUM, TK ;

HOPKINS, PB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :2703-2709

[12] PROTIODESILYLATION REACTIONS OF BETA-HYDROXYSILANES AND GAMMA-HYDROXYSILANES - DEUTERIUM LABELING AND SILICON-DIRECTED EPOXIDE OPENINGS [J].

HUDRLIK, PF ;

HOLMES, PE ;

HUDRLIK, AM .

TETRAHEDRON LETTERS, 1988, 29 (49) :6395-6398

[13] PROTIODESILYLATION REACTIONS OF SIMPLE BETA-HYDROXYSILANES (AND ALPHA-HYDROXYSILANES) - HOMO-BROOK REARRANGEMENTS [J].

HUDRLIK, PF ;

HUDRLIK, AM ;

KULKARNI, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6809-6811

[14] Effects of FK317, a novel anti-cancer agent, on survival of mice bearing B16BL6 melanoma and Lewis lung carcinoma [J].

Inami, M ;

Kawamura, I ;

Tsujimoto, S ;

Nishigaki, F ;

Matsumoto, S ;

Naoe, Y ;

Sasakawa, Y ;

Matsuo, M ;

Manda, T ;

Goto, T .

CANCER LETTERS, 2002, 181 (01) :39-45

[15] ENANTIOSPECIFIC SYNTHESIS OF AN AZIRIDINOBENZOAZOCINONE, AN ADVANCED INTERMEDIATE CONTAINING THE CORE NUCLEUS OF FR900482 AND FK973 [J].

JONES, RJ ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) :1144-1146

[16]

Judd T. C., 2002, ANGEW CHEM, V114, P4877

[17] Concise enantioselective synthesis of (+)-FR66979 and (+)-FR900482: Dimethyldioxirane-mediated construction of the hydroxylamine hemiketal [J].

Judd, TC ;

Williams, RM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4683-4685

[18] Synthesis and DNA cross-linking of a phototriggered FR900482 mitosene progenitor [J].

Judd, TC ;

Williams, RM .

ORGANIC LETTERS, 2002, 4 (21) :3711-3714

[19] Intramolecular 1,3-dipolar cycloaddition strategy for enantioselective synthesis of FR-900482 analogues [J].

Kambe, M ;

Arai, E ;

Suzuki, M ;

Tokuyama, H ;

Fukuyama, T .

ORGANIC LETTERS, 2001, 3 (16) :2575-2578

[20] Total synthesis of an enantiomeric pair of FR900482 .3. Completion of the synthesis by assembling the two segments [J].

Katoh, T ;

Nagata, Y ;

Yoshino, T ;

Nakatani, S ;

Terashima, S .

TETRAHEDRON, 1997, 53 (30) :10253-10270

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