Diversity-Oriented Synthesis
of Functionalized Polyheterocycles from Garner Aldehyde

Ajay Kumar Srivastava; Heebum Song; Seung Bum Park

doi:10.1055/s-0030-1260069

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Synthesis 2011(14): 2215-2222
DOI: 10.1055/s-0030-1260069

SPECIALTOPIC

Diversity-Oriented Synthesis of Functionalized Polyheterocycles from Garner Aldehyde

Ajay Kumar Srivastava^a, Heebum Song^a, Seung Bum Park*^a,b
^a Department of Chemistry, Seoul National University, Seoul 151-747, Korea
^b Department of Biophysics and Chemical Biology, Seoul National University, Seoul 151-747, Korea
Fax: +82(2)8844025; e-Mail: sbpark@snu.ac.kr;

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Publikationsverlauf

Received 9 April 2011
Publikationsdatum:
15. Juni 2011 (online)

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Abstract

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.

Key words

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

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