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Catalytic Asymmetric Aldol Equivalents for an Enantioselective Total Synthesis of Apoptolidin C

Vargo, Thomas R. Catalytic Asymmetric Aldol Equivalents for an Enantioselective Total Synthesis of Apoptolidin C. Doctoral Dissertation, University of Pittsburgh.

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    Abstract

    Apoptolidin C is a biologically active polypropionate macrolide isolated from the soil bacteria Nocardiopsis sp. The work presented herein highlights a novel approach to synthesizing the core of the natural product, apoptolidinone C, as well as a de-novo synthesis of the C9 sacharide. Our synthesis utilizes a catalytic asymmetric approach to the construction of the complex polypropionate arrays contained in apoptolidin through the use of our acyl halide-aldehyde cyclocondensation (AAC) reaction. Employing the AAC technology using cinchona alkaloid derived catalysts, as well as the complementary chiral aluminum catalysts, we have successfully demonstrated a catalytic and asymmetric synthesis of the aglycone core of apoptolidin C. In addition, we have demonstrated the asymmetric synthesis of the C9 saccharide from achiral starting materials.

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    Details

    Item Type: University of Pittsburgh ETD
    ETD Committee:
    ETD Committee TypeCommittee MemberEmail
    Thesis AdvisorNelson, Scott G.sgnelson@pitt.edu
    Committee MemberFloreancig, Paul E.florean@pitt.edu
    Committee MemberWilcox, Craigdaylite@pitt.edu
    Committee MemberZhang, Linzhanglx@upmc.edu
    Title: Catalytic Asymmetric Aldol Equivalents for an Enantioselective Total Synthesis of Apoptolidin C
    Status: Published
    Abstract: Apoptolidin C is a biologically active polypropionate macrolide isolated from the soil bacteria Nocardiopsis sp. The work presented herein highlights a novel approach to synthesizing the core of the natural product, apoptolidinone C, as well as a de-novo synthesis of the C9 sacharide. Our synthesis utilizes a catalytic asymmetric approach to the construction of the complex polypropionate arrays contained in apoptolidin through the use of our acyl halide-aldehyde cyclocondensation (AAC) reaction. Employing the AAC technology using cinchona alkaloid derived catalysts, as well as the complementary chiral aluminum catalysts, we have successfully demonstrated a catalytic and asymmetric synthesis of the aglycone core of apoptolidin C. In addition, we have demonstrated the asymmetric synthesis of the C9 saccharide from achiral starting materials.
    Defense Date: 31 October 2011
    Approval Date: 01 February 2012
    Submission Date: 01 November 2011
    Release Date: 01 February 2012
    Access Restriction: No restriction; Release the ETD for access worldwide immediately.
    Patent pending: No
    Number of Pages: 174
    Institution: University of Pittsburgh
    Thesis Type: Doctoral Dissertation
    Refereed: Yes
    Degree: PhD - Doctor of Philosophy
    Uncontrolled Keywords: Organic Synthesis Natural Product
    Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
    Date Deposited: 01 Feb 2012 10:13
    Last Modified: 02 Feb 2012 01:15

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