Method for the stereocontrolled synthesis of stegobinone and use

Details Method for the stereocontrolled synthesis of stegobinone and use Method for the stereocontrolled synthesis of stegobinone and use

1995-08-02

1997-10-28

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Borate esters

549416, C07F 502

Patent

active

056819781

ABSTRACT:
A method of synthesis of (2S,3R,1'R)-stegobinone(I) using borane intermediates and methods for the use of stegobinone (I) for attracting beetles of the Anobium species.

REFERENCES:
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Griffith, W.P., et al. (1987) "Preparation and use of Tetra-n-butylammonium Per-ruthenate (TBAP reagent) and Tetr-n-propylammonium Per-ruthenate (TPAP reagent) as New Catalytic Oxidants for Alcohols, " J. Chem. Soc., Chem. Commun. 21:1625-7.
Kodama, H., et al., (1987) "Stegobiol, A New Sex Phermone Component of Drugstore Beetle (Segobium paniceum L.), " J. Chem. Ecol. 13:1871-1879.
Kuwahara, Y., et al., (1978) "Chemical Studies on the Anobiidae: Sex Pheromone of the Drugstore Beetle, Stegobium paniceum (L.) (Coleoptera), " Tetrahedron 34:1769-1774.
Matteson, D.S., and Man, H.-W., "High-Precision Asymmetric Synthesis of Stegobiol of Stegobinone via Bornic Esters," (1993) J. Org. Chem. 58:6545-6547.
Matteson, D.S., et al., (1990) "Synthesis of Assymetrically Deuterated Glycerol and Dibenzylglyceraldehyde via Boronic Esters," J. Am. Chem. Soc. 112:3964-3969.
Ware, J.C., and Taylor, T.G., (1963) "Electrophilic Substitution. Chromic Acid Cleavage of Carbon-Boron Bonds, " J. Am. Chem. Soc. 85:3026-7.
White, P.R., and Birch, M.C., (1987) "Female Sex Phermone of the Common Furniture Beetle Anobium punctatum (Coleoptera: Anobiidae): Extraction, Identification and Bioassays, " Chem. Ecol. 13:1695-1706.

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