TY  - UNPB
ID  - pittir8229
UR  - http://d-scholarship-dev.library.pitt.edu/8229/
A1  - Rosenberg, Adam Jason
TI  - Progress Towards the Total Synthesis of 3?-Hydroxy-15-Rippertene
Y1  - 2009/09/29/
N2  - 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 3?-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.
AV  - public
KW  - Pauson-Khand; Rippertene; Synthesis
ER  -