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Formal Synthesis of (±)‐Mitsugashiwalactone and (±)‐Isodihydronepetalactone from Norborn‐5‐en‐2‐one Involving Shapiro Reaction

 

作者: Meng‐Yang Chang,   Nein‐Chen Ciang,  

 

期刊: Journal of the Chinese Chemical Society  （WILEY Available online 1999）
卷期: Volume 46, issue 1  

页码: 41-45

 

ISSN:0009-4536

 

年代: 1999

 

DOI:10.1002/jccs.199900005

 

出版商: WILEY‐VCH Verlag

 

关键词: Iridoid;Mitsugashiwalactone;Isodihydronepetalactone;Dihydronepetalactone;Onikulactone;Shapiro reaction;Baeyer‐Villiger oxidation

 

数据来源: WILEY

 

摘要:

AbstractA formal synthesis of (±)‐mitsugashiwalactone (1) and (±)‐isodihydro nepetalactone (2) was accomplished. Baeyer‐Villiger lactonization of ketone9followed by acidic treatment led to the rearranged lactone8, which underwent a series of functional group transformations to give cyclopentanone derivatives19and20. Shapiro reaction on21and22in the presence of excess dry ice gave lactones5and6. Lactones5and6previously have been converted to mitsugashiwalactone (1) and isodihydronepetalactone (2), respe

 

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