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Implementation of Catalytic, Asymmetric Technology Toward the Total Synthesis of Apoptolidin C

Hale, James (2012) Implementation of Catalytic, Asymmetric Technology Toward the Total Synthesis of Apoptolidin C. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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The total synthesis of apoptolidin C (3), a highly selective cytotoxic macrolide, has been under investigation in our lab. Work completed includes the synthesis of the C1-C11 fragment 29, the macrocyclic core 3b, and the disaccharide subunit 31. These goals have been realized utilizing catalytic, asymmetric reaction methodology including the acyl halide-aldehyde cyclocondensation (AAC) and proline catalyzed dimerization of simple aldehyde starting materials 33-38.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Hale, Jamesjsh30@pitt.eduJSH30
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scottsgnelson@pitt.eduSGNELSON
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Committee MemberKoide, Kazunorikoide@pitt.eduKOIDE
Committee MemberGold, Barrygoldbi@pitt.eduGOLDBI
Date: 18 June 2012
Date Type: Publication
Defense Date: 30 March 2012
Approval Date: 18 June 2012
Submission Date: 4 April 2012
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 178
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: total synthesis, organic chemistry, apoptolidin c, aac, acyl halide-aldehyde cyclocondensation
Date Deposited: 18 Jun 2012 17:59
Last Modified: 15 Nov 2016 13:57


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