Approaches toward the enantioselective total synthesis of amarogentic
Doctoral Thesis
2001
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University of Cape Town
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Abstract
Three different, but complementary strategies for the enantioselective synthesis of the secoiridoid core of amarogentin were evaluated. The first is based on the enantioselective desymmetrisation of meso-anhydrides using titanium TADDOLates. 1,2,4,6-Tetrahydrophthalic anhydride was desymmetrised and chemoselectively reduced to give (3aR, 7aS)-3a,4,7,7a-Tetrahydro-3H-isobenzofuran-1-one. Further development of this route was performed on a racemic model.
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Includes bibliographical references.
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Stevens, A. 2001. Approaches toward the enantioselective total synthesis of amarogentic. University of Cape Town.