The first total synthesis of ingenol [electronic resource].
- Chemistry, Organic
- Local subjects:
Penn dissertations -- Chemistry.
Chemistry -- Penn dissertations.
- System Details:
- Mode of access: World Wide Web.
- Ingenol is a tetracyclic diterpene polyol which was originally isolated from plants of the Euphorbiaceae family. The synthetic appeal of this densely functionalized natural product can be attributed to both the unique molecular architecture and the diverse biological activity.*
This dissertation depicts the first total synthesis of ingenol which comprises nearly two decades of research. The most notable feature of this synthesis is construction of the "In-Out" tricycle through implementation of the novel [2+2] dioxenone photocycloaddition/retroaldol fragmentation methodology. Also, the high degree of oxygenation located along the lower hemisphere of the molecule was installed in a highly efficient manner. The total synthesis was completed in 38 steps, with an average yield per step of 82% and an overall yield of 0.06%.
*Please see dissertation for diagram.
- Thesis (Ph.D. in Chemistry) -- University of Pennsylvania, 2003.
Source: Dissertation Abstracts International, Volume: 64-04, Section: B, page: 1738.
Supervisor: Jeffrey D. Winkler.
- Local notes:
- School code: 0175.
- Winkler, Jeffrey D., advisor
University of Pennsylvania.
- Contained In:
- Dissertation Abstracts International 64-04B.
- Access Restriction:
- Restricted for use by site license.
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