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Catalytic Asymmetric Synthesis of Complex Polypropionates:A Synthesis of Erythronolide B

Chandra, Binita (2010) Catalytic Asymmetric Synthesis of Complex Polypropionates:A Synthesis of Erythronolide B. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Studies towards the total synthesis of the polypropionate macrolide agycone Erythronolide B have been presented. Catalytic asymmetric AAC methodology has been applied to efficiently generate the C10-C13 and the C4-C5 stereocenters in the polypropionate fragments 105 and 209 through â-lactones 76, 80, and 86 respectively. An efficient installation of the C2 and C3-stereocenters in 193 was realized through a Lewis-base catalyzed Mukaiyama aldol reaction. Finally, a highly stereoselective aldol coupling of fragments 105 and 209 was used to join the fragments together.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Chandra, Binitabic3@pitt.eduBIC3
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scott
Committee MemberDoemling, Alexander
Committee MemberWilcox, Craig S
Committee MemberMeyer, Tara
Date: 28 January 2010
Date Type: Completion
Defense Date: 8 December 2009
Approval Date: 28 January 2010
Submission Date: 15 November 2009
Access Restriction: 5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
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: macrolide synthesis; polypropionates; stereotetrad; AAC; erythronolide B
Other ID:, etd-11152009-132712
Date Deposited: 10 Nov 2011 20:04
Last Modified: 15 Nov 2016 13:51


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