Steroidal Sapogenins. XXXIX.<sup>1</sup> Transformations in Ring-C of the Sapogenin Series

Zderic, John A.; Carpio, Humberto; Limón, Dinorah Chávez; Ruiz, Augusto

doi:10.1021/jo01066a053

Cited by 8 publications

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“…The analytical sample, obtained by crystallization from petroleum ether (b.p. 30-60°), had the same melting range; infrared: "1™ 3.20 µ, 6.08 µ, and 11.20 µ (> C=CH2), 3.62 µ and 5.83 µ (-CHO), 5.89 µ (> C=0).…”

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confidence: 91%

“…The fact that this type of compound will serve almost as well as the n-butylthiomethylene derivative in the reduction-acid rearrangement sequence is documented.15 However, the reduction of this oxygen analog is complicated by a significant amount of 1,4-reduction. Thus, the infrared spectrum of the reduction product of the ketone (3) with lithium aluminum hydride indicated the presence of a saturated ketone. In view of the basic work-up used in this reaction, this ketone could not have arisen from ketal hydrolysis.…”

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confidence: 99%

“…The solution to this problem was found by using the isopropoxymethylene group,14 which can be introduced under basic reaction conditions. Thus, by first hydroxymethylation of the ketal ketone (2) and then treatment of the resulting derivative with isopropyl iodide and potassium carbonate in acetone solution, there resulted an 85% over-all yield of the desired isopropoxymethylene derivative (3).…”

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Experiments Directed toward the Total Synthesis of Terpenes. II. The Synthesis of dl-6-Keto-5,5, 9-trimethyl-2-methylene-trans-decalyl-lα-acetic Acid and Derivatives¹

Church¹,

Ireland²,

Marshall³

1962

J. Org. Chem.

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l-(9-Anthryl)-l,2-dihydro-8,6-pyridazinedione (6b) by rearrangement of 6,ll-dihydro-6,ll-o-benzenopyridazino[l,2-b\phthalazine-l ,4-dione (4b). A solution of 4b, (1.33 g.), glacial acetic acid (50 ml.), and coned, hydrochloric acid (3 ml.) was stirred at room temperature for 4 hr. The yellow precipitate which formed was removed by filtration, and washed with acetic acid and water. It amounted to 1.24 g. (93%) of 6b which was obtained pure, as yellow cubes, m.p. > 300°, after a single crystallization from dimethylformamide-water. In the infrared, 6b exhibited H-stretching absorption (broad, weak, ambiguous) at 2960-2340 cm.-1, acyl absorption at 1661 cm.-1, and intense absorption at 1563 and 1497 cm.-1. In the ultraviolet (0.02 N sodium hydroxide), 6b had Xmax 252 (e 148,000), 333 (« 5300), 348 (e 7800), 365 (« 10,700), and 385 mM (e 9100) and Xmin 226 (e 23,300), 282 (<= 1300), 336 (« 5300), 355 (e 6400), and 375 m/i (e5100). It was soluble in 0.01 N sodium hydroxide.

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confidence: 91%

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confidence: 99%

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confidence: 99%

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Experiments Directed toward the Total Synthesis of Terpenes. II. The Synthesis of dl-6-Keto-5,5, 9-trimethyl-2-methylene-trans-decalyl-lα-acetic Acid and Derivatives¹

Church¹,

Ireland²,

Marshall³

1962

J. Org. Chem.

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“…The monomeric nature of "EtMgCl" in tetrahydrofuran implies that the species in solution are (1) EtMgCl, (2) a mixture of Et2Mg and MgCl2, or (3) an equilibrium mixture of ( 1) and ( 2). The possibility of ( 2) seems unlikely since a 2 M solution of "EtMgCl" did not precipitate MgCl2 on standing although the solubility limit of MgCl2 in tetrahydrofuran is only 0.5 M. Confirmation of the lack of association of the predominant species in solution was given by the observation that both Et2Mg and MgCl2 were found to be monomeric in tetrahydrofuran.…”

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confidence: 99%