METABOLISM OF PROGESTERONE BY
            <i>CYLINDROCARPON RADICICOLA</i>
            AND
            <i>STREPTOMYCES LAVENDULAE</i>

Peterson, Glen E.; Thoma, R. W.; Perlman, D.; Fried, Josef

doi:10.1128/jb.74.5.684-688.1957

Cited by 32 publications

(4 citation statements)

References 8 publications

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“…Caled for CnH2oN403: C, 62.19; , 6.10; N, 17.09. Found: C, 62.25; , 6.21; H, 17.39. Tetrahydrofarinosin (7).-A solution of 2 g of farinosin in 200 ml of acetic acid was heated under reflux while 10 g of zinc dust was added. After heating for 24 hr, the solution was filtered and the solvent evaporated.…”

Section: Methodsmentioning

confidence: 99%

“…The infrared (6) Because encelin was much less abundant in the plant than farinosin, most of the chemical manipulations were performed with material prepared by the dehydration of farinosin. (7) The peak at m/e 91 is present in the mass spectra of all of the sesquiterpenoid lactones that have been studied in this laboratory. It probably represents the tropylium ion, C7H7+.…”

mentioning

confidence: 95%

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Sesquiterpene lactones of Encelia farinosa

Geissman¹,

Mukherjee²

1968

J. Org. Chem.

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methanol in ether (2 1.) and 5% methanol in ether (0.5 1.) provided, after evaporation to dryness, a grayish gum which solidified upon trituration with ether (XIX, 387 mg). The solid product showed A , , 2.80, 2.90 (broad and intense), 5.78, 6.00, 6.20 p ; Xf-. 236 mp.The mixture of diols was then utilized as such. A4-Etiojervene-3,11,17-trione (=I).-A mixture of the epimeric diols (XIX, 25 mg) was oxidized with chromic acid (20 mg) in glacial acetic acid (10 ml) and water (1 ml) at room temperature for a period of 4 hr. The reaction mixture was poured over cracked ice and was extracted with chloroform (30 ml). The chloroform layer was washed with a saturated sodium bicarbonate solution, water, and was then dried over anhydrous sodium sulfate. Evaporation of the chloroform gave a brownish solid which was crystallized from acetone-petroleum ether to provide needles of XXI: mp 214216'; XmX 5.78, 5.85, 6.00, 6.20 p (superimposable upon that of the authentic sample); A , 236 mp (e 15,500); mixture melting point with the authentic sample was undepressed .A~-l7-Ethyletiojerven-l7~-o1-3,ll,2O-trione (C-Nor-D-homo-11-keto-17a-hydroxyprogesterone) (XX) and A4-17-Ethyletiojerven-17fl-ol-3,ll ,ZO-trione (C-Nor-D-homo-11-keto-178-hydroxyprogesterone) (XXII). Method A.-To a stirred solution of XI (700 mg, mp 164-165') in t-butyl alcohol under a nitrogen atmosphere wrw added a solution of 1.5 M H202 (4 ml) in t-butyl alcohol (5 ml), followed by a solution of osmium tetroxide (25 mg) in t-butyl alcohol (10 ml) which was added slowly over a period of 1 hr. Stirring was continued for 48 hr, after which was added a solution of sodium sulfite (0.7 g) in water (5 ml) and the stirring was continued for an additional 15 min. Water was added and the reaction mixture was extracted with ether (0.5 1.). The ethereal extract was washed with water and dried over anhydrous sodium sulfate. Evaporation of the ether to dryness gave a solid (0.95 9).Column chromatography of the residue on silica gel (30 g) packed in benzene and elution with chloroform-benzene mixtures (up to 50% CHCls, 2 1.) gave starting material (300 mg). Further elution with chloroform-benzene (1: l, l l.) provided, after evaporation to dryness, a white solid (280 mg, mp 208-212') composed mainly of X X . Crystallization from chloroformpetroleum ether gave white needles: mp 215-216'; [u]*~D 4-54' (e 0.52); XmsI 2.85 (weak), 5.78, 5.84, 6.00, 6.20 p; Xmnx 236 mp (e 17,100); ORD [+]Ek f17411'; -17360'; a = -. 2 6 7 ' . --. . Anal. Calcd for C&&: C, 73.22; H, 8.19. Found: C, 73.28; H, 8.45. Continued elution with chloroform (1 1.) yielded a white solid (250 mg, mp 225-232') composed mainly of XXII. Crystallization from chloroform-petroleum ether afforded colorless plates: mp 230-235' dec; [a]*'D +56" (C 0.43);

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 95%

Sesquiterpene lactones of Encelia farinosa

Geissman¹,

Mukherjee²

1968

J. Org. Chem.

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show abstract

“…Relative Reactivities of Hydrocarbons toward IBD," Molecular Chlorine, and ¿-Butyl Hypochlorite 1.00 1.26 ± 0.06 (2) 0.60 ±0.09 (4) 0.84 ±0.05 (3) " Numbers in parentheses indicate the number of independent experiments carried out. 6 Errors indicate average deviations from the mean values reported.…”

Section: Table VImentioning

confidence: 99%

“…for the Halogenation of 1-Chloropropane and ji-Butyronitrile'* (40°, Photoinitiation, CCfi Solvent)•Isomer distribution, %Values are averages of the results of three or more independent experiments 6. Taken from ref 7.…”

mentioning

confidence: 99%