[3+2]-cycloaddition reactions of 2-phenyliodonio-1,3-dioxacyclohexanemethylide: Facile synthesis of fused dihydrofuran derivatives

被引：44

作者：

Asouti, A ^{[1
]}

Hadjiarapoglou, LP ^{[1
]}

机构：

[1] Univ Ioannina, Dept Chem, Sect Organ Chem, GR-45110 Ioannina, Greece

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 49期

关键词：

iodonium ylide; 3+2]-cycloaddition; dihydrofuran;

D O I：

10.1016/S0040-4039(98)01997-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodonium ylide 2, derived from 1,3-cyclohexadione, undergoes thermal [3+2]-cycloaddition with acetonirile, carbon disulfide and p, P'- dimethoxythiobenzophenone with Cu(acac)(2) catalysis to form the corresponding 5-membered heterocycles and alkene respectively. Photochemically 2 reacts with various alkenes and dienes to form dihydrofuran derivatives, key intermediates for paniculide A, B and pentalene synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9073 / 9076

页数：4

共 34 条

[1] ALLISON AJ, 1968, J CHEM SOC CHEM COMM, P1493
[2] SYNTHESIS OF PANICULIDE-B AND PANICULIDE-C
BAKER, R
GIBSON, CL
SWAIN, CJ
TAPOLCZAY, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07): : 1509 - 1516
[3] SESQUITERPENE LACTONES - TOTAL SYNTHESIS OF (+/-)-ERIOLANIN AND (+/-)-ERIOLANGIN
GRIECO, PA
OGURI, T
GILMAN, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) : 5886 - 5891
[4] TOTAL SYNTHESIS OF (+/-)-ERIOLANIN
GRIECO, PA
OGURI, T
GILMAN, S
DETITTA, GT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (05) : 1616 - 1618
[5] HADJARAPOGLOU L, 1985, J AM CHEM SOC, V108, P7178
[6] 2,3-dihydro-3-oxo-2-phenyliodonium-benzo[b]thiolenide-1,1-dioxide: Synthesis, decomposition and Cu-catalyzed thermal reactions.
Hadjiarapoglou, LP
Schank, K
[J]. TETRAHEDRON, 1997, 53 (27) : 9365 - 9376
[7] THE CHEMISTRY OF PHOTOLYTICALLY AND THERMALLY GENERATED ALPHA-KETOCARBENES FROM IODONIUM YLIDES OF BETA-DIKETONES
HADJIARAPOGLOU, LP
[J]. TETRAHEDRON LETTERS, 1987, 28 (38) : 4449 - 4450
[8] HAYASI Y, 1979, B CHEM SOC JPN, V43, P2506
[9] TOTAL SYNTHESIS OF (+/-)-PANICULIDE-A
JACOBI, PA
KACZMAREK, CSR
UDODONG, UE
[J]. TETRAHEDRON, 1987, 43 (23) : 5475 - 5488
[10] NEW ACCESS TO DL-PANICULIDE-A USING ALPHA-PHENYLTHIO-BETA-VINYLBUTENOLIDE AS SYNTHETIC BLOCK
KIDO, F
NODA, Y
YOSHIKOSHI, A
[J]. TETRAHEDRON, 1987, 43 (23) : 5467 - 5474

← 1 2 3 4 →