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A 1,3-Dipolar Cycloaddition Approach to the Synthesis of Resiniferatoxin

Loyer-Drew, Jennifer (2008) A 1,3-Dipolar Cycloaddition Approach to the Synthesis of Resiniferatoxin. Master's Thesis, University of Pittsburgh. (Unpublished)

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The Rh(I)-catalyzed allenic cyclocarbonylation reaction is a formal [2 + 2 + 1] cycloaddition process that has been used to gain access to 4-alkylidenecyclopentenones. Incorporation of a six-membered ring on the tether between the allene and the alkyne components allows access to a variety of [6-7-5] ring structures featured in the skeletons of various natural products, including resiniferatoxin. This thesis describes the development of two systems, each with a future synthesis of resiniferatoxin in mind. First, a model system was designed to demonstrate the compatibility of the isoxazoline moiety with the Rh(I)-catalyzed cyclocarbonylation reaction. The second investigation involved the synthesis of an asymmetrically functionalized 2-cyclohexenone in order to attempt a stereoselective 1,3-dipolar cycloaddition. The first model system successfully led to the synthesis of the unfunctionalized [6-7-5] core of resiniferatoxin via cyclocarbonylation of an isoxazoline-containing allene-yne. Unfortunately, under numerous conditions, the functionalized cyclohexenone synthesized for the second study failed to undergo [2 + 3] cycloaddition with a nitrile oxide.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Loyer-Drew, Jenniferjal61@pitt.eduJAL61
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairBrummond, Kay Mkbrummon@pitt.eduKBRUMMON
Committee MemberCurran, Dennis Pcurran@pitt.eduCURRAN
Committee MemberMeyer, Tara Ytmeyer@pitt.eduTMEYER
Date: 28 September 2008
Date Type: Completion
Defense Date: 31 July 2008
Approval Date: 28 September 2008
Submission Date: 18 July 2008
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: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: cycloaddition; cyclocarbonylation; daphnane; nitrile oxide; Pauson-Khand; resiniferatoxin
Other ID:, etd-07182008-135945
Date Deposited: 10 Nov 2011 19:52
Last Modified: 15 Nov 2016 13:46


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