Total Syntheses of (-)- and (+)-Goniomitine

被引：62

作者：

Mizutani, Masaya ^{[1
]}

Inagaki, Fuyuhiko ^{[1
]}

Nakanishi, Takeo ^{[1
]}

Yanagihara, Chihiro ^{[1
]}

Tamai, Ikumi ^{[1
]}

Mukai, Chisato ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 07期

关键词：

ASPIDOSPERMIDINE; ALLENYLSTANNANES; GONIOMITINE; DERIVATIVES; ALDEHYDES; ADDITIONS; ALCOHOLS; ENOLATE;

D O I：

10.1021/ol200320z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Stille coupling reaction of 3-(benzyloxymethyl)-1-(tert-butyldiphenylsiloxy)ethyl-1-(tributylstannyl)allene with N-(tert-butoxycarbonyl)-2-iodoaniline directly produced the corresponding 2-vinylindole derivative, which was Independently transformed into natural (-)-goniomitine and unnatural (+)-goniomitine via the cross-metathesis with chiral oxazolopiperidone lactams. The antiproliferative activity of the synthesized natural (-)-goniomitine in Mock and MDCK/MDR1 cells showed them to be more potent to retard cell growth than unnatural (+)-goniomitine.

引用

收藏

页码：1796 / 1799

页数：4

相关论文

共 13 条

[1] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine [J].

Amat, M ;

Bosch, J ;

Hidalgo, J ;

Cantó, M ;

Pérez, M ;

Llor, N ;

Molins, E ;

Miravitlles, C ;

Orozco, M ;

Luque, J .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3074-3084

[2] Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams [J].

Amat, Mercedes ;

Lozano, Oscar ;

Escolano, Carmen ;

Molins, Elies ;

Bosch, Joan .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) :4431-4439

[3] Catalytic Selective Cyclizations of Aminocyclopropanes: Formal Synthesis of Aspidospermidine and Total Synthesis of Goniomitine [J].

De Simone, Filippo ;

Gertsch, Juerg ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (33) :5767-5770

[4] Synthetic applications of 2-(1,3-dithian-2-yl)indoles .7. Synthesis of aspidospermidine [J].

Forns, P ;

Diez, A ;

Rubiralta, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7882-7888

[5] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].

Garber, SB ;

Kingsbury, JS ;

Gray, BL ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179

[6] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].

GRIECO, PA ;

GILMAN, S ;

NISHIZAWA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486

[7] SYNTHESIS OF ENANTIOENRICHED HOMOPROPARGYLIC ALCOHOLS THROUGH DIASTEREOSELECTIVE-SE' ADDITIONS OF CHIRAL ALLENYLSTANNANES TO ALDEHYDES [J].

MARSHALL, JA ;

WANG, XJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1242-1252

[8] DIASTEREOSELECTIVE ADDITIONS OF ALLENYLSTANNANES TO ALDEHYDES [J].

MARSHALL, JA ;

WANG, XJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6246-6248

[9] Preparation of chiral allenylmetal reagents from enantioenriched allenyl iodides and propargylic mesylates. A comparison of indium, bismuth, and tin derivatives [J].

Marshall, JA ;

Grant, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8214-8219

[10] Total synthesis of (±)-goniomitine via a formal nitrile/donor-acceptor cyclopropane [3+2] cyclization [J].

Morales, Christian L. ;

Pagenkopf, Brian L. .

ORGANIC LETTERS, 2008, 10 (02) :157-159