Construction of Chiral Tertiary Alcohol Stereocenters via the [2,3]- Meisenheimer Rearrangement: Enantioselective Synthesis of the Side-Chain Acids of Homoharringtonine and Harringtonine

✍ Scribed by Yang, Hua; Sun, Moran; Zhao, Shuguang; Zhu, Ming; Xie, Yangla; Niu, Changling; Li, Chunlin

• Book ID: 118265046
• Publisher: American Chemical Society
• Year: 2012
• Tongue: English
• Weight: 645 KB
• Volume: 78
• Category: Article
• ISSN: 0022-3263
• DOI: 10.1021/jo302203g

✦ Synopsis

For the first time, the [2,3]-Meisenheimer rearrangement has been developed into a general strategy for the construction of chiral tertiary alcohols. The effectiveness and practicality of this methodology are illustrated by the successful synthesis of (R)-20 and (R)-30, the side chain acids of homoharringtonine and harringtonine, respectively.