SYNTHETIC STUDIES OF MARINE ALKALOIDS HAPALINDOLES .2. LITHIUM ALUMINUM-HYDRIDE REDUCTION OF THE ELECTRON-RICH CARBON-CARBON DOUBLE-BOND CONJUGATED WITH THE INDOLE NUCLEUS

被引：22

作者：

MURATAKE, H ^{[1
]}

NATSUME, M ^{[1
]}

机构：

[1] RES FDN ITSUU LAB,2-28-10 TAMAGAWA,SETAGAYA KU,TOKYO 158,JAPAN

来源：

TETRAHEDRON | 1990年 / 46卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(01)96006-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

- A reaction mechanism is proposed for an unusual, reduction of the electron-rich C-C double bond with lithium aluminum hydride in the indole derivatives such as 3. Liberation of an aluminum hydride anion from 1-indolylaluminum intermediates, i.e., 27 may play an important role for the inversion of the polarity at the 15 position. © 1990.

引用

页码：6343 / 6350

页数：8

共 6 条

[1] STEREOCHEMISTRY AND MECHANISM OF CARBON-CARBON DOUBLE-BOND REDUCTION IN METHYL CINNAMATE BY LITHIUM ALUMINUM HYDRIDE
SNYDER, EI
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (11): : 3531 - &
[2] CARBON-CARBON BOND-CLEAVAGE DURING LITHIUM ALUMINUM-HYDRIDE REDUCTION OF A TERMINAL PROPARGYL ALCOHOL
CANE, DE
IYENGAR, R
TETRAHEDRON LETTERS, 1979, (31) : 2871 - 2874
[3] ANOMALOUS LITHIUM ALUMINUM-HYDRIDE REDUCTION OF CARBON-CARBON DOUBLE-BONDS IN 7-AZABICYCLO[2.2.1]HEPTENYL SYSTEMS
MARCHAND, AP
ALLEN, RW
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1974, : 22 - 22
[4] ANOMALOUS LITHIUM ALUMINUM-HYDRIDE REDUCTION OF CARBON-CARBON DOUBLE-BONDS IN 7-AZABICYCLO(2.2.1)HEPTENYL SYSTEMS
MARCHAND, AP
ALLEN, RW
TETRAHEDRON LETTERS, 1975, (01) : 67 - 70
[5] Use of indium hydride (Cl2InH) for chemoselective reduction of the carbon-carbon double bond in conjugated alkenes
Ranu, BC
Samanta, S
TETRAHEDRON LETTERS, 2002, 43 (41) : 7405 - 7407
[6] SAFE ONE-POT CARBON-CARBON BOND FORMATION WITH LITHIATED NITROSAMINES INCLUDING DENITROSATION BY SEQUENTIAL REDUCTION WITH LITHIUM ALUMINUM-HYDRIDE AND RANEY-NICKEL
SEEBACH, D
WYKYPIEL, W
SYNTHESIS-STUTTGART, 1979, (06): : 423 - 424

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