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

doi:10.3390/50400674

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Molecules 2000, 5(4), 674-698; doi:10.3390/50400674

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

Veljko Dragojlovic

Oceanographic Center, Nova Southeastern University, 8000 North Ocean Drive, Dania, 33004, USA

Received: 14 March 2000 / Accepted: 14 April 2000 / Published: 20 April 2000

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Abstract: 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.

Keywords: Subergorgic acid; sesquiterpenoid synthesis; methylenecyclopentane annulation; bifunctional reagents; triquinane synthesis

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MDPI and ACS Style

Dragojlovic, V. Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues. Molecules 2000, 5, 674-698.

AMA Style

Dragojlovic V. Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues. Molecules. 2000; 5(4):674-698.

Chicago/Turabian Style

Dragojlovic, Veljko. 2000. "Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues." Molecules 5, no. 4: 674-698.

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