The ether-benzene (6:4) eluate gave 66 mg. of testololactone (Rt 0.25).Conversion of Testosterone by A. tamarii.-Testosterone (1.00 g.) was incubated with A. tamarii for 48 hr. as previously described and the usual work-up gave 877 mg. of crude product; the t.l.c. showed three spots (R¡ 0.43, 0.25, and 0.09). The crude extract was chromatographed on 20 g. of Merck acid-washed alumina (activity IV); the benzene eluate gave 624 mg. of noncrystalline material, the t.l.c. of which showed two spots of Rt 0.43 and 0.25, corresponding, respectively, to testosterone and testololactone. Recrystallization of the combined chromatography fractions from benzene gave, after drying at 0.1 mm., 210 mg. of pure testosterone, m.p. 149-151°. Rechromatography of the residue from the recrystallization on 35 g. of Merck acid-washed alumina (activity IV) gave 363 mg. of pure testololactone, m.p. 205-207°, Rt 0.25. The ether-benzene (8:2) eluate gave 217 mg. of 119-hydroxytestosterone, m.p. 238-240°, Rt 0.09, identical in all respects with that obtained as previously described.
Insgesamt 28 Diole des Typs (II) und 61 Benzodioxincarbonsäuren(‐säureester) des Typs (IV) wurden auf verschiedenen Wegen dargestellt, darunter RU 24728 (IVa) (trans bezüglich der Gruppen ‐Ph und ‐COOH), RU 25247 (IVb) (trans) und 25961 (IVd) (trans), und auf ihre hypolipämische Aktivität untersucht.
Treatment of vinyl carbinols la,b with triethyl orthoacrylate (2) and excess propionic acid in refluxing toluene gives the -propionoxymethyl esters 8a,b as major products along with minor amounts of the a-ethoxymethyl esters 7a,b. Similar treatment of ethynyl carbinol 13 affords allenic diester 14 (major) and ether ester 15 (minor). The diesters 8a,b yielded the -methylene esters 9a,b upon exposure to l,5-diazabicyclo[4.3.0]non-5-ene (DBN) in refluxing benzene. When 14 was treated with DBN, the Diels-Alder dimer 17 resulted. Mechanistic considerations involving the Claisen rearrangements are presented.
Das Trimethyl‐hydrochinon (Ia) liefert über das Diacetat (Ib) bei der Friesschen Verschiebung die Acetophenone (II), die zu (III) peracetyliert werden.
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