Diversity-Oriented Synthesis of Functionalized Polyheterocycles from Garner Aldehyde

作者：Srivastava Ajay Kumar; Song Heebum; Park Seung Bum^*

来源：Synthesis, 2011, (14): 2215-2222.

DOI：10.1055/s-0030-1260069

• diversity-oriented synthesis
• Garner aldehyde
• isobenzofuran
• isoindole
• isoquinoline

We report a diversity-oriented synthesis of diverse drug-like polyheterocycles from Garner aldehyde derived 1-hydroxy-1,3-dihydroisobenzofuran 20 as a key intermediate. The oxonium-mediated nucleophilic addition of 20 in the presence of boron trifluoride-diethyl ether complex provided enantiopure 1,3-disubstituted 1,3-dihydroisobenzofurans through 1,3-asymmetric induction. Further diversification of 20 allowed the diastereoselective syntheses of drug-like polyheterocycles including the 3-substituted isobenzofuran-1(3H)-one, 2,3-dihydro-1H-isoindol-1-one, and 3,4-disubstituted dihydroisoquinolinone ring systems.

• 出版日期2011-7