Naphthalene 1.2.3.4- tetrahydro-6-hydroxy

Work on the Mills-Nixon effect has been reviewed by Badger [2]. Most of the experimental work done in this field has involved a study of relative chemical reactivities and hence is subject to the severe limitations mentioned earlier [ lc]. From a study of the ease with which the benzoates of isomeric hydroxy-5,6,7,8-tetrahydroacetonaphthones underwent the Baker-Venkataraman transformation O Farrell et ah [3] recently concluded that the 1,2-bond of 5,6,7,8-tetrahydro-naphthalene has a higher bond order than the 2,3-bond. Similar work also led these authors to conclude that the 4,5-bond in indan is of higher order than the 5,6-bond. These workers did not attempt to assess the extent of the difference in bond order presumably exhibited by the bonds in question. 

Condensation of 7-methoxy-3,4-dihydro-1(2H)-naphthal-enone with tetramethylene dibromide by means of NaH in benzene or tert amyl alcohol gives 3,4-dihydro-7-methoxy-2,2-tetramethylene-1(2H)-naphthalene (bp (0,05 mbar) 120-123 °C), which is treated with acetonitrile and butyllithium in THF yielding 1-hydroxy-7-methoxy-1,2,3,4-tetrahydro-2,2-tetramethylene-1-naphthalene-acetonitrile (mp 140-142 °C). This compound is reduced with LiAIH4 in THF to afford hydro-2,2-tetramethylene-1-naphthol (mp 178-180 °C), and isomerized to 4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxy-phenantrene i (mp 187 °C). 

Pravastatin was isolated as products of enzymatic hydroxylation by some kinds of microorganisms of [lS-[l-a(R ),7p,8P(2S, 4S )8a 3]]-2-methylbutanoic acid l,2,3,7,8,8a-hexahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2))-pyran-2-yl)ethyl]-l-naphthalenic lactone (campactin) or their carboxylic acid or their salts (products of animal metabolism of microorganisms from the genera Nocardia, Streptomyces et cetera). 

HYDROXY-3-(1,2,3,4-TETRAHYDRO-3-(4-(4-(TRIFLUOROMETHYL)PHEN-OXY) PHENYL)-1-NAPHTHALEN-YL)2H-1 -BENZOPYR AN-2-ONE mf C32H23F3O4 mw 528.55 SAFETY PROFILE A poison by ingesdon. When heated to decomposidon it emits toxic vapors of F". 

The same reaction is observed between /ran5-l-hydroxy-2-hydroperoxy-l,2,3,4-tetrahydro-naphthalene and aldehydes or ketones in the presence of catalytic amounts of Amberlyst-15 or trimethylsilyl trifluoromethanesulfonate the rranj-fused trioxanes being formed in 75-95% yield <92C114>. 

Sikkimotoxin, 3a,4,9,9a-Tetrahydro-4-hydroxy-6,7-dunethoxy-9-(3,4,S-trimethoxyphenyt)naphtho 2,3-c -furan-I(3H) >ne 1 -hydroxy-2-hydroxymethyl-6,7-dimeth -oxy-4-(3 4 5 -trim ethoxy phenyl)-1,2,3,4-let rahydro-naphthalene-3-carboxylic acid lactone, C Hj p, mol wt 430.44. C 64.17%, H 6.09%, O 29.74%. Isoln from roots and rhizomes of Podophyllum sikkimeitsis R. Chatterjee et Mukerjee, Berberidaceae Chatterjee. Datta, Indian J. Physiol Allied Set 4, 6l (1950). Structnre Chatterjee. Chakra-varti, J. Am. Pharm. Assoc. Scl Ed. 4l, 415 (1952) Schreier, Helv. Chim. Acta 47, 1529 (1964). 

Tetrahydrofuran ring. An aq. soln. of l,2-dihydro-2-hydroxy-7-methoxy-czs-l,2-dimethyl-l-(2-dimethylaminoethyl)naphthalene methiodide digested 20 min. with thallous hydroxide on a steam bath -> l,2,3a,9b-tetrahydro-8-methoxy-czs-3a,9b-dimethylnaphtho[24-b]furan. Y 78%.—Thallous hydroxide proved to be superior to silver hydroxide. F. e. s. E. L. May and H. Kugita, J. Org. Ghem. 26,188 (1961). 

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