A Flexible Approach to (S)-5-Alkyl Tetramic Acid Derivatives:  Application to the Asymmetric Synthesis of (+)-Preussin and Protected (3S,4S)-AHPPA

A flexible asymmetric approach to 5-alkyl tetramic acid derivatives is described, which is based on the use of 9 as the first synthetic equivalent to chiral nonracemic tetramic acid 5-carbanionic synthon 9b. The existence of the carbanion intermediate 9b was proven by trapping with trimethylchlorosi...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 5; no. 23; pp. 4341 - 4344
Main Authors Huang, Pei-Qiang, Wu, Tian-Jun, Ruan, Yuan-Ping
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.11.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTIFUNGAL AGENT (+)-PREUSSIN
DIELS-ALDER REACTIONS
ENANTIOSELECTIVE SYNTHESIS
ANTIBIOTIC (+)-PREUSSIN
EFFICIENT SYNTHESIS
STEREOSPECIFIC SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
VINYLOGOUS URETHANE APPROACH
CONCISE SYNTHESIS
OKADAIC ACID
Online AccessGet full text

Cover

More Information
Summary:A flexible asymmetric approach to 5-alkyl tetramic acid derivatives is described, which is based on the use of 9 as the first synthetic equivalent to chiral nonracemic tetramic acid 5-carbanionic synthon 9b. The existence of the carbanion intermediate 9b was proven by trapping with trimethylchlorosilane. Application of the present method to the synthesis of antifungal alkaloid (+)-preussin, as well as protected (3S,4S)-AHPPA 6, is also described.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035617a