DIASTEREOSELECTIVE [2,3]-WITTIG REARRANGEMENT OF A TERTIARY BISALLYLIC ETHER

被引：5

作者：

SHI, XW

WEBSTER, FX

KALLMERTEN, J

MEINWALD, J

机构：

[1] SYRACUSE UNIV, SYRACUSE, NY 13244 USA

[2] CORNELL UNIV, ITHACA, NY 14853 USA

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 40期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(95)01500-H

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective [2,3]-Wittig rearrangement of a tertiary bisallylic ether (8) is described. The stereochemical outcomes for rearranged products were determined. The effects of reaction conditions on selectivities were investigated. Matsuccocus female sex pheromones 1-3 were efficiently synthesized via this rearrangement.

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页码：7197 / 7200

页数：4

相关论文

共 18 条

[1] DIASTEREOSELECTIVE [2,3] WITTIG REARRANGEMENT OF TERTIARY ALPHA-LITHIO ETHERS [J].

BALESTRA, M ;

KALLMERTEN, J .

TETRAHEDRON LETTERS, 1988, 29 (52) :6901-6904

[2] THE [2,3] WITTIG REARRANGEMENT OF TERTIARY ALLYLIC ETHERS - APPLICATION TO THE SYNTHESIS OF THE C12-C25 SUBUNIT OF ZINCOPHORIN [J].

BALESTRA, M ;

WITTMAN, MD ;

KALLMERTEN, J .

TETRAHEDRON LETTERS, 1988, 29 (52) :6905-6908

[3]

COUTTS SJ, 1990, TETRAHEDRON LETT, V31, P4310

[4] IDENTIFICATION OF THE FEMALE SEX-PHEROMONE OF THE ISRAELI PINE BAST SCALE MATSUCOCCUS-JOSEPHI [J].

DUNKELBLUM, E ;

MENDEL, Z ;

ASSAEL, F ;

HAREL, M ;

KERHOAS, L ;

EINHORN, J .

TETRAHEDRON LETTERS, 1993, 34 (17) :2805-2808

[5] IDENTIFICATION OF THE SEX-PHEROMONE OF THE MARITIME PINE SCALE MATSUCOCCUS-FEYTAUDI [J].

EINHORN, J ;

MENASSIEU, P ;

MALOSSE, C ;

DUCROT, PH .

TETRAHEDRON LETTERS, 1990, 31 (46) :6633-6636

[6] [2,3]-WITTIG REARRANGEMENT ON CARBOHYDRATE TEMPLATE - NOVEL-APPROACH TO CHIRAL SYNTHESIS OF 3-ALKYLMALIC ACIDS [J].

KAKINUMA, K ;

LI, HY .

TETRAHEDRON LETTERS, 1989, 30 (31) :4157-4160

[7] IDENTIFICATION OF THE SEX-PHEROMONE OF 3 MATSUCOCCUS PINE BAST SCALES [J].

LANIER, GN ;

QI, YT ;

WEST, JR ;

PARK, SC ;

WEBSTER, FX ;

SILVERSTEIN, RM .

JOURNAL OF CHEMICAL ECOLOGY, 1989, 15 (05) :1645-1659

[8] ENANTIOSELECTIVE SYNTHESIS OF ALL 4 STEREOISOMERS OF (2E,4E)-4,6,10,12-TETRAMETHYL-2,4-TRIDECADIEN-7-ONE, THE SEX-PHEROMONE OF MATSUCOCCUS PINE BAST SCALE [J].

LIN, GQ ;

XU, WC .

TETRAHEDRON LETTERS, 1993, 34 (37) :5931-5934

[9]

MIKAMI K, 1991, SYNTHESIS-STUTTGART, P594

[10]

MORI K, 1993, LIEBIGS ANN CHEM, P993, DOI 10.1002/jlac.1993199301158