Enantioselective Total Synthesis of (+)-Azimine and (+)-Carpaine

The enantioselective total syntheses of (+)-azimine and (+)-carpaine have been developed, starting with (S)-1,2,4-butanetriol as a single source of chirality. The key common feature in these syntheses involves stereoselective intramolecular hetero-Diels−Alder reaction of an acylnitroso compound. The...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 21; pp. 3839 - 3842
Main Authors Sato, Taro, Aoyagi, Sakae, Kibayashi, Chihiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.10.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
(+/-)-CARPAMIC ACID
CYCLOADDITION
CASSINE SERIES
PIPERIDINE
STEREOSELECTIVE TOTAL SYNTHESIS
DIELS-ALDER REACTION
CONFIGURATION
LACTONIZATION
CARPAINE
ALKALOIDS
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Summary:The enantioselective total syntheses of (+)-azimine and (+)-carpaine have been developed, starting with (S)-1,2,4-butanetriol as a single source of chirality. The key common feature in these syntheses involves stereoselective intramolecular hetero-Diels−Alder reaction of an acylnitroso compound. The critical macrocyclic dilactonization of the N-Cbz derivatives of azimic acid and carpamic acid was efficiently achieved by using the Yamguchi macrocyclization conditions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol030088w