Total Synthesis of (±)-Kainic Acid: A Photochemical C–H Carbamoylation Approach

A novel photochemical C–H carbamoylation of an octahydroisoindole derivative with PhNCO has allowed the authors to provide a unique access to a highly functionalized proline motif from which total synthesis of (±)-kainic acid, a bioactive marine alkaloid, has been accomplished.

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 13; no. 10; pp. 2674 - 2677
Main Authors Kamon, Takuma, Irifune, Yayoi, Tanaka, Tetsuaki, Yoshimitsu, Takehiko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.05.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Kainic Acid - analogs & derivatives
Kainic Acid - chemical synthesis
Kainic Acid - chemistry
Marine Biology
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
PAUSON-KHAND REACTION
(-)-KAINIC ACID
ENANTIOSELECTIVE SYNTHESIS
STEREOCONTROLLED TOTAL-SYNTHESIS
(-)-ALPHA-KAINIC ACID
ALPHA-KAINIC ACID
PHOTOINDUCED-ELECTRON-TRANSFER
(+)-ALPHA-ALLOKAINIC ACID
ASYMMETRIC TOTAL-SYNTHESIS
EXCITATORY AMINO-ACIDS
Online AccessGet full text

Cover

More Information
Summary:A novel photochemical C–H carbamoylation of an octahydroisoindole derivative with PhNCO has allowed the authors to provide a unique access to a highly functionalized proline motif from which total synthesis of (±)-kainic acid, a bioactive marine alkaloid, has been accomplished.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200772f