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

Vargo, Thomas R. (2012) Catalytic Asymmetric Aldol Equivalents for an Enantioselective Total Synthesis of Apoptolidin C. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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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
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Vargo, Thomas R.thomas.vargo@gmail.com
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Thesis AdvisorNelson, Scott G.sgnelson@pitt.eduSGNELSON
Committee MemberFloreancig, Paul E.florean@pitt.eduFLOREAN
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Committee MemberZhang, Linzhanglx@upmc.eduLIZ22
Date: 1 February 2012
Date Type: Publication
Defense Date: 31 October 2011
Approval Date: 1 February 2012
Submission Date: 1 November 2011
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 174
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: Organic Synthesis Natural Product
Date Deposited: 01 Feb 2012 15:13
Last Modified: 19 Dec 2016 14:34
URI: http://d-scholarship.pitt.edu/id/eprint/6166

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