Heliquinomycin, a member of a rubromycin family of natural products, is a complex natural product consisting of a naphthoquinone and an isocoumarin which are linked through a 5,6-spiroketal functionality. The spiroketal also bears a glycosidic linkage. Previous work in our group has developed a method for generating both the naphthoquinone and isocoumarin portions of this natural product. The focus of this work was to develop a method for joining these two halves of the natural product while also allowing for the formation of the spiroketal. The specific goals accomplished include developing a method for extending the allyl-side chain of a model isocoumarin compound, functionalization of an olefin in preparation for forming the spiroketal structure and coupling of the naphthoquinone with the isocoumarin model via a nitrile-oxide [3+2] dipolar cycloaddition.
Completion of the natural product will also require several oxidation state adjustments of the naphthoquinone moiety. To that end we were able to carry out the necessary transformations: opening an isoxazole ring, reduction of a quinone ring to an acetylated hydroquinone and oxidation of a trimethoxybenzene ring to a methoxy quinone in attempting a synthesis of the natural product Y-1005.
| Identifer | oai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/20647 |
| Date | January 2007 |
| Creators | Schaefer, Amber Rakowitz |
| Contributors | Behar, Victor |
| Source Sets | Rice University |
| Language | English |
| Detected Language | English |
| Type | Thesis, Text |
| Format | 172 p., application/pdf |
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