Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form
D-Scholarship @ Pitt Banner and Links to Homepage

Efforts Towards the Total Synthesis of Amphidinolide B

Gopalarathnam, Apsara (2007) Efforts Towards the Total Synthesis of Amphidinolide B. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

[img]
Preview
 PDF
Primary Text
Download (916kB) | Preview

Abstract

Studies towards the total synthesis of the cytotoxic marine macrolide Amphidinolide B have been disclosed. Catalytic asymmetric AAC methodology has been applied to efficiently generate the C11- and the C18- stereocenters in the requisite fragments 114 and 120 throughƒnbeta-lactones 102 and 81 respectively.An efficient route to install the C14-C15 trisubstituted alkene was realized through a stannylcupration reaction. The Stille and Suzuki cross-coupling methodologies were investigated for the formation of the C13-C15 diene of amphidinolide B. Iodide 90 was coupled with boronic ester 114 via an efficient Suzuki reaction to form a C7-C20 fragment 115. Fragment was further homologated and coupled to sulfone 65 to complete a C1-C20 synthon of amphidinolide B.

Share

Citation/Export:
Social Networking:
Share |

Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Gopalarathnam, Apsaraapg16@pitt.eduAPG16
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scott Gsgnelson@pitt.eduSGNELSON
Committee MemberCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberJohnson, J. Karl
Committee MemberFloreancig, Paul Eflorean@pitt.eduFLOREAN
Date: 29 January 2007
Date Type: Completion
Defense Date: 5 September 2006
Approval Date: 29 January 2007
Submission Date: 7 September 2006
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
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: cytotoxic activity; exocyclic diene
Other ID: http://etd.library.pitt.edu/ETD/available/etd-09072006-203459/, etd-09072006-203459
Date Deposited: 10 Nov 2011 20:01
Last Modified: 15 Nov 2016 13:50
URI: http://d-scholarship.pitt.edu/id/eprint/9337

Metrics

Monthly Views for the past 3 years

Plum Analytics

Actions (login required)

View Item View Item