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Progress Towards the Total Synthesis of 3α-Hydroxy-15-Rippertene

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Rosenberg, Adam Jason (2009) Progress Towards the Total Synthesis of 3α-Hydroxy-15-Rippertene. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

The Rh(I)-catalyzed allenic cyclocarbonylation reaction is a formal [2 + 2 + 1] cyclocarbonylation process that has been used to gain access to 4-alkylidenecyclopentenones. Inclusion 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 found in the core-skeletons of natural products such as rippertene. This thesis describes a synthetic approach to the carbocyclic skeleton of 3α-hydroxy-15-rippertene, utilizing the Rh(I)-catalyzed allenic cyclocarbonylation reaction. Starting from 2-butyn-1-ol the [6-7-5] carbocyclic core of rippertene was synthesized in 1.9% over 10 steps.


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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Rosenberg, Adam Jasonadam.j.rosenberg@gmail.com
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairBrummond, Kay M.kbrummon@pitt.eduKBRUMMON
Committee MemberCurran, Dennis P.curran@pitt.eduCURRAN
Committee MemberFloreancig, Paul E.florean@pitt.eduFLOREAN
Date: 29 September 2009
Date Type: Completion
Defense Date: 26 May 2009
Approval Date: 29 September 2009
Submission Date: 29 June 2009
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: Pauson-Khand; Rippertene; Synthesis
Other ID: http://etd.library.pitt.edu/ETD/available/etd-06292009-092407/, etd-06292009-092407
Date Deposited: 10 Nov 2011 19:49
Last Modified: 15 Nov 2016 13:45
URI: http://d-scholarship.pitt.edu/id/eprint/8229

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