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A Hetero Diels-alder Approach to the Synthesis of Castanospermine Analogs: Preparation of 1-O-ethyl-1,6,8a-triepicastanospermine

 

作者: Panagiotis Kefalas,   Henri-Philippe Husson,   DavidS. Grierson,  

 

期刊: Natural Product Letters  （Taylor Available online 1993）
卷期: Volume 3, issue 4  

页码: 313-318

 

ISSN:1057-5634

 

年代: 1993

 

DOI:10.1080/10575639308043882

 

出版商: Taylor & Francis Group

 

关键词: Castanospermine;hetero Diels-Alder reaction;dihydro-2H-1,2-oxazine

 

数据来源: Taylor

 

摘要:

Hetero Diels-Alder reaction of diene7, obtained in four steps from aldehyde4, with Troc-NO8produced the dihydro-2H-1,2-oxazine9in 48% yield. Conversion of this intermediate to the N-deprotected tosylate10followed by ring closure gave the bicyclic product11which was converted to the indolizidine derivative13by N‒O bond cleavage (H2, RaNi) and recyclization under Mitsunobu conditions. Final deprotection of13with mild acid gave the target triepicastanospermine analog3.

 

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