Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues

Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide - dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane di...

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Bibliographic Details
Published in:MolBank 2000-04, Vol.5 (4), p.674-698
Main Author: Dragojlovic, Veljko
Format: Article
Language:English
Subjects:
Acids
bifunctional reagents
methylenecyclopentane annulation
Natural products
Potassium
Reagents
sesquiterpenoid synthesis
Subergorgic acid
Toxicity
triquinane synthesis
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Summary:Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide - dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane dienedione (9) by means of an 8-step sequence.
ISSN:1420-3049
1420-3049
1422-8599
DOI:10.3390/50400674