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(Unpublished)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.
Share
| Citation/Export: |
|
| Social Networking: |
|
Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
|
| 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 |
Metrics
Monthly Views for the past 3 years
Plum Analytics
Actions (login required)
 |
View Item |
![[feed]](/images/feed-icon-32x32.png){kind=icon}