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Synthesis of Natural and Non-Natural Polycylic Alkaloids

Hoye, Adam Thomas (2010) Synthesis of Natural and Non-Natural Polycylic Alkaloids. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Part one of this dissertation describes the synthesis of novel polycyclic natural product-like compounds from dicyclopropylmethylamine starting materials. Using methodology previously developed in our group, products from the initial one-pot multicomponent reaction via the rearrangement of a bicyclo[1.1.0]butane intermediate were successfully transformed into polycyclic systems. These small, medium and large heterocycles mimic complex alkaloids found in nature, and were further elaborated to incorporate additional functionalities.Part two describes our investigation into the parvistemonine class of Stemona alkaloids. We developed a unified strategy to target several related Stemona natural products. A [3,3]-sigmatropic rearrangement was used to relay key stereochemical information across the characteristic pyrrolo[1,2-a]azepine core of these molecules and install contiguous stereocenters in a controlled fashion. This approach produced advanced intermediates towards the syntheses of parvistemonine and sessilifoliamides B and D, and culminated in the first enantioselective total syntheses of sessilifoliamide C and 8-epi-stemoamide.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Hoye, Adam Thomasath7@pitt.eduATH7
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberDay, Billybday@pitt.eduBDAY
Committee MemberCurran, Denniscurran@pitt.eduCURRAN
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Date: 30 September 2010
Date Type: Completion
Defense Date: 16 August 2010
Approval Date: 30 September 2010
Submission Date: 9 August 2010
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: biosynthetic relationship; cyclodehydration/reduction; Eschenmoser-Claisen; hydroindoline; indole; Ireland-Claisen; Johnson-Claisen; organozirconium; orthoester; stenine; transmetallation; tuberostemonine; tuberostemonone; ring-closing metathesis; total synthesis
Other ID:, etd-08092010-110833
Date Deposited: 10 Nov 2011 19:58
Last Modified: 15 Nov 2016 13:48


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