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Synthetic Studies of Meloscine and Related Alkaloids

Zhang, Hanmo (2013) Synthetic Studies of Meloscine and Related Alkaloids. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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The first section of this dissertation describes the discovery and studies of new radical desulfonylation reactions. These reactions allow convenient access to structurally diverse imines under mild conditions. We have examined several related desulfonylation reactions, and the results of this investigation support the general mechanism that we initially proposed.
The second section details the synthesis of (±)-epimeloscine, (±)-meloscine, and analogs. The invention of a novel, cascade radical annulation of divinylcyclopropanes enables expedient synthesis of (±)-epimeloscine and (±)-meloscine, and analogs. Preliminary studies on a chirality transfer approach towards (+)-meloscine are discussed. This approach delivered only moderate chirality transfer, however, a new cascade cope/ene reaction was discovered along the way.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Zhang, Hanmohaz14@pitt.eduHAZ14
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberFloreancig, Paul Eflorean@pitt.eduFLOREAN
Committee MemberWilcox, Craig Sdaylite@pitt.eduDAYLITE
Committee MemberDay, Billy Wbday@pitt.eduBDAY
Date: 2 July 2013
Date Type: Publication
Defense Date: 28 February 2013
Approval Date: 2 July 2013
Submission Date: 27 March 2013
Access Restriction: 3 year -- Restrict access to University of Pittsburgh for a period of 3 years.
Number of Pages: 215
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: imine-forming reaction; desulfonylation; alkaloid synthesis; cascade radical annulation; divinylcyclopropane; memory of chirality; cope/ene reaction
Date Deposited: 02 Jul 2013 17:58
Last Modified: 15 Nov 2016 14:10


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