Efficient synthesis of vinyl chlorides and/or gem-dichlorides from ketones by treatment with tungsten hexachloride

Author:

Jung Michael E.,Wasserman Jacob I.

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference18 articles.

1. Isolation of dichlorolissoclimide: (a) Malochet-Grivois, C.; Cotelle, P.; Baird, J. F.; Henichart, J. P.; Debitus, C.; Roussakis, C.; Verbist, J.-F. Tetrahedron Lett. 1991, 32, 6701–6702. Isolation of chlorolissoclimide: (b) Baird, J. F.; Malochet-Grivois, C.; Roussakis, C.; Cotelle, P.; Henichart, J. P.; Debitus, C.; Verbist, J.-F. Nat. Prod. Lett. 1994, 4, 43–50. Crystal structure of dichlorolissoclimide: (c) Toupet, L.; Biard, J. F.; Verbist, J.-F. J. Nat. Prod. 1996, 59, 1203–1204. Biological Activity: (d) Roussakis, C.; Charrier, J.; Riou, D.; Biard, J. F.; Malochet, C.; Meflah, K.; Verbist, J.-F. Anti-Cancer Drug Design 1994, 9, 119–128 and references cited therein.

2. Isolation of reticulidins: (a) Wratten, S. J.; Faulkner, D. J. Tetrahedron Lett. 1978, 16, 1395–1398; (b) Simpson, J. S.; Raniga, P.; Garson, M. J. Tetrahedron Lett. 1997, 38, 7947–7950; (c) Tanaka, J.; Higa, T. J. Nat. Prod. 1999, 62, 1339–1340; (d) Musman, M.; Tanaka, J.; Higa, T. J. Nat. Prod. 2001, 64, 111–113.

3. Haterumaimides J and K, Potent Cytotoxic Diterpene Alkaloids from the AscidianLissoclinumSpecies

4. Tungsten hexachloride has been utilized in several procedures such as the dehydration of epoxides to olefins (Umbreit, M. A.; Sharpless, K. B. Org. Synth. 1981, 60, 29–34) and more recently the chlorination of alcohols (Coe, E. M.; Jones, C. J. Polyhedron 1992, 11, 3123–3128). Also see Ref. 11.

5. Synthesis of (+-)-Geosmin. Part 1. On the Synthesis and Epoxidation of 1,4a-Dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one.

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