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

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

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 Subergorgic acid; sesquiterpenoid synthesis; methylenecyclopentane annulation; bifunctional reagents; triquinane synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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