Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1993-08-09
1995-07-18
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C07C 6702
Patent
active
054343003
ABSTRACT:
The method is directed to the preparation of dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan from sclareol using an alkoxy-radical fragmentation reaction. A novel 9-haloethyl decalin derivative is an intermediate in this method.
REFERENCES:
patent: 3029255 (1962-04-01), Stoll
patent: 3050532 (1962-08-01), Schumacher
Urones, J. G. et al., "Functionalization of C-12 in Labdanic Diterpenes: Synthesis of the Natural Diterpenic Lactones from Cistus Ladaniferus, L." Tetrahedron Letters 26:5717-5720 (1985).
Majerski, Z. et al., "Hypoidite Thermolysis-Cyclization Reaction: Convenient Synthesis of 4-Homoprotoadamantan-4-one from 3-Homoadamantanol", J. Chem. Soc. 13:478-479 (1977).
Houben-Weyl, Methoden der Organischen Chemie, IV/b:939-952 (1975).
Varvoglis et al., "Polyvalent Iodine Compounds in Organic Synthesis", Synthesis, 704-726, Sep. 1984.
Buchi, G., et al. "Terpenes 1X. The Conversion of Sclareol to Manool", Croatica Chemica Acta. 29:163-171 (1957).
Bigley et al.; "Synthesis of Diterpenes, Part III. The Synthesis, and Configuratioin at Position 13, of Diterpenes of the Labdane Group", J. Chem. Soc., 4613-4627 (1960).
Cambie et al. "XXX. Conversion of 8alpha, 13-epoxylabd-14-ene into a compound with an Ambergris Type Odour" Aust.J. Chem., 24, 583-591 (1971).
Corey et al.; "Synthesis of a B-Amyrin Derivative, Olean-11, 12; 13, 18-diene," J. Am. Chem. Soc., 85, 3979-3982 (1963).
Hinder and Stoll; (170. Odeur et constitution IV) "Sur les epoxydes hydroaromatiques a odeur ambree"; Helv. Chim. Acta, 33, 1308-1312 (1950).
Jegou et al.; "Ambergris Revisited. Isolation of Volatile Constitutents, Identification and Synthesis of Ambra-Aldehyde C.sub.14 H.sup.22 O"; Nouv. J. Chem., 1, 529-531 (1977).
Ruzika et al., "Zur Kenntnis der Diterpene", Helv. Chim. Acta, 25, 621-629 (1942).
Stoll and Hinder, (161, "Odeur et Constitution III) Les Substances Bicyclohomofarnesiques"; Helv. Chim. Acta, 33, 1251-1260 (1950).
Bedoukian, "Violet Fragrance Compounds", in Fragrance Chemistry: The Science of the Sense of Smell, E. T. Thieman ed. Academic Press, (1982).
Ohloff, "The Fragrance of Ambergris", in Fragrance Chemistry: The Science of the Sense of Smell, E. T. Thieman ed. Academic Press, (1982).
Bensadoun et al., "Stereoelectronic Control in the Beta-Fragmentation Reactions of Alkoxyl Radicals, An Empirical Predictive Rule", J. Chem. Research (s). 236-237 (1981).
Ohloff et al., "New Ambra Odorants by Photoreactions of 15, 16-Dinorlabd-8(20)--en-13-one", Helv. Chim. Acta, 59:75-81 (1976).
Demole and Wuest, "Synthesis stereoselectives de deux trioxydes C.sub.18 H.sub.30 O.sub.3 stereo-isomers d'ambreindolide et de sclareol-lactone a partir de derives du (t)-manool", Helv. Chim. Acta. 50:1314-1327 (1967).
Ohloff et al., 18 "Conformation-Odor Relationships in Norlabane Oxides," Helv. Chim. Acta, 69:163-173 (1986).
Ohloff et al., 212 "Significance of the Geminal Dimethyl Group in the Odor Principle of Ambrox", Helv. Chim. Acta, 68:2022-2029 (1985).
Ohloff et al., (205. Stereochemistry), "Odor Relationships in Enantiomeric Ambergris Fragrances", Helv. Chim. Acta. 63:1932-1946 (1980).
Hinder and Stoll, (246. Odeur et constitution IX). "Preparation de substances bicyclohomofarnesigues stereoisomeres", Helv. Chim. Acta. 36:1995-2008 (1953).
Grant et al., "The Diterpenes of Dacrydium Kirkii. A Synthesis of Labdonae-7alpha 13-Diol", Aust. J. Chem., 25:365-374 (1972).
Stoll et al., (198. Synthesis d'epoxydes hydroaromatiques IX). "Action du gazchlorhydrique sur let (tetramethyl-1,1,6,10-hydroxy-6-decalyl-5-ethanol)", Helv. Chim. Acta, 34:1664-1667 (1951).
Criegee, "Oxidations with Lead Tetraacetate", in Oxidation in Organic Chemistry pp. 276-305, Kenneth B. Wiberg ed., Acad. Press (1965).
Mihailovic and Cekovic, "Intramolecular Oxidative Cyclization of Alcohols with Lead Tetraacetate", Synthesis, No. 5:209-224 (1970).
Schreiber et al., "Iron/Copper Promoted Fragmentation Reactions of alpha-Alkoxy Hydroperoxides", Tetrahedron, 42:2445-2950 (1986).
H. O. House, "Dissolving Metal Reduction and Related Reaction," in Modern Synthetic Reactions, pp. 145-205. (Benjamin/Cummings Publishing Co., 1972).
Conrad, III Joseph M.
Dees Jos,e G.
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