Reactions of methylenecyclopropanes with a diethylzinc-bromoform system, and the utilization for synthesis of a novel cyclopropylidene-nucleoside

被引：20

作者：

Cheng, CM

Shimo, T

Somekawa, K ^{[1
]}

Kawaminami, M

机构：

[1] Kagoshima Univ, Fac Engn, Dept Chem Engn & Appl Chem, Kagoshima 890, Japan

[2] Kagoshima Univ, Fac Sci, Dept Phys, Kagoshima 890, Japan

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(97)10406-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of substituted methylenecyclopropane with diethylzinc-bromoform gave bromospiro[2.2]pentane derivatives, bromoform-addition compounds, an oxabicyclo-compound and adjacent dibromo-compound, and the last product was derived to a novel alpha,beta-unsaturated nucloside. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：9005 / 9008

页数：4

相关论文

共 9 条

[1]

AKHACHINSKAYA TV, 1989, ZH ORG KHIM+, V25, P1645

[2] SYNTHESIS OF CYCLOPROPANE DERIVATIVES - PRECURSORS FOR DIMETHYLENECYCLOPROPANE AND TRIMETHYLENECYCLOPROPANE [J].

BLOMQUIST, AT ;

LONGONE, DT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (08) :2012-2017

[3] HYDROCARBON THERMAL DEGENERATE REARRANGEMENTS .4. STEREOCHEMISTRY OF METHYLENECYCLOPROPANE SELF-INTERCONVERSION - CHIRAL AND ACHIRAL INTERMEDIATES [J].

GAJEWSKI, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (18) :4450-&

[4] EFFICIENT SYNTHESES OF PROTECTED (2S,3S)-2,3-BIS(HYDROXYMETHYL)CYCLOBUTANONE, KEY INTERMEDIATES FOR THE SYNTHESIS OF CHIRAL CARBOCYCLIC ANALOGS OF OXETANOCIN [J].

HSIAO, CN ;

HANNICK, SM .

TETRAHEDRON LETTERS, 1990, 31 (46) :6609-6612

[5] SYNTHETIC STUDIES ON HIGHLY MODIFIED NUCLEOSIDES DIRECTED TOWARDS CREATION OF ANTI-HIV AGENTS [J].

KATAGIRI, N .

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1993, 113 (04) :285-306

[6] OXYGEN-ACCELERATED GENERATION OF BROMOCARBENOID REAGENT OF ZINC FROM DIETHYLZINC AND BROMOFORM - BROMOCYCLOPROPANES FROM OLEFINS [J].

MIYANO, S ;

HASHIMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (12) :3665-3668

[7]

NISHIYAMA Y, 1989, J ANTIBIOT, V12, P5925

[8] SYNTHESIS OF (+/-)-CYCLOPROP-G, THE CYCLOPROPYL ANALOG OF THE BROAD-SPECTRUM ANTIVIRAL AGENT CYCLOBUT-G [J].

NORBECK, DW ;

SHAM, HL ;

HERRIN, T ;

ROSENBROOK, W ;

PLATTNER, JJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (02) :128-129

[9] NUCLEIC-ACID DERIVED ALLENOLS - UNUSUAL ANALOGS OF NUCLEOSIDES WITH ANTIRETROVIRAL ACTIVITY [J].

PHADTARE, S ;

ZEMLICKA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5925-5931