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(Unpublished)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Unpublished |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