ChemInform Abstract: Asymmetric Syntheses of Lignans Utilizing Novel Diastereoselective Michael Addition of Cyanohydrin: Syntheses of (+)-Fargesin and (-)- Picropodophyllone.

✍ Scribed by S. YOSHIDA; T. YAMANAKA; T. MIYAKE; Y. MORITANI; H. OHMIZU; T. IWASAKI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199750276

✦ Synopsis

Asymmetric Syntheses of Lignans Utilizing Novel Diastereoselective Michael Addition of Cyanohydrin: Syntheses of (+)-Fargesin and (-)-Picropodophyllone.

-The key step in the synthesis of the title compounds (+)-(V) and (-)-( XII) is diastereoselective Michael addition of the cyanohydrin (I) to the cis-esters (S)-and (R)-(II). Additionally, it is shown that addition of (I) to a trans-ester proceeds with low diastereoselectivity.