Efficient and economic asymmetric synthesis of nootkatone,...

Details Efficient and economic asymmetric synthesis of nootkatone,... Efficient and economic asymmetric synthesis of nootkatone,...

2006-09-26

2006-09-26

Witherspoon, Sikarl A. (Department: 1621)

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

Organic compounds

Oxygen containing

C568S374000, C568S819000, C568S820000

Reexamination Certificate

active

07112700

ABSTRACT:
An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed. The starting materials used in the synthesis are inexpensive. The principal starting material, (−)-β-Pinene, is on the GRAS list (generally recognized as safe).

REFERENCES:
patent: 3819711 (1974-06-01), Bozzato
Marshall, J. et al., “The Total Synthesis of Racemic Isonootkatone (α-Vetivone),”Chem. Commun., pp. 753-754 (1967).
Revial, G. et al., “Enantioselective synthesis of (+)-α-vetivone through the Michael reaction of chiral amines,”Tetrahedron: Asymmetry, vol. 11, pp. 4975-4983 (2000).
Torii, S. et al., “Functionalization of trans-decalin. V. A synthesis of (±)-nootkatone and (±)-valencene from 4β,4aβ-dimethyl-Δ6,7-octalin-1-one ethylene acetal,”Bull. Chem. Soc. Jpn., vol. 55, pp. 887-890 (1982).
van der Gen, A. et al., “Stereoselective synthesis of eremophilane sesquiterpenoids from β-pinene,”Recueil Trav. Chim. Pays-Bas, vol. 90, pp. 1034-1044 (1971).
Yanami, T. et al., “Synthetic Study of (+)-Nootkatone from (−)-β-Pinene,”J. Organic Chem., vol. 45, pp. 607-612 (1980).

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