ChemInform Abstract: VOLLSYNTH. DES ERSTEN TYPS VON A,B‐INDOLOSTEROIDEN

Sladkov, V. I.; Shner, V. F.; Алексеева, Л. М.; Turchin, K. F.; Анисимова, О. С.; Sheinker, Yu. N.; Суворов, Н. Н.

doi:10.1002/chin.197137391

Chemischer Informationsdienst. Organische Chemie

1971

DOI: 10.1002/chin.197137391

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ChemInform Abstract: VOLLSYNTH. DES ERSTEN TYPS VON A,B‐INDOLOSTEROIDEN

V. I. Sladkov¹,

V. F. Shner²,

Л. М. Алексеева³

et al.

Abstract: Als Ausgangsprodukt dient 3‐Phenyl‐2‐(carboxymethyl)‐2‐cyclopenten‐1‐on (I), aus dem über die Stufen (II)‐(VII) das tricyclische Amin (VIII) gewonnen wird.

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1974

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“…The first example of a steroid containing the indole ring system was synthesized from a BD intermediate [23]. Demethoxy 8 (Scheme 11-2) was converted via 28 and 29 into 30 (Scheme 11-5).…”

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B + D → Bd → BCD → Abcd

1974

Organic Chemistry: A Series of Monographs

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In Chapter 4 syntheses were described in which ring D was attached to an AB moiety, following which ring C was closed producing the steroid. In theory it should be just as feasible to connect B and D by one of the many routes delineated in Chapter 4, close ring C, then construct ring A by one of several available annotation methods. In practice, however, this approach has enjoyed only very limited success.One of the few successful syntheses began with the triketone 1 (Scheme 11-1), which was obtained by Michael addition of 1,3-cyclohexanedione to methyl vinyl ketone [1], The next step was to add carbons 11 and 12 by a Grignard reaction with vinylmagnesium bromide. To protect oxo groups at C-3 and C-5 (steroid numbering) from attack by the Grignard reagents, 1 was converted to the corresponding chromone (temporary closure of ring A) by heating in acetic anhydride. The Grignard reaction and subsequent hydrolysis gave 2 in 24% yield [2,3]. Michael addition of 2-methyl-l,3-cyclohexanedione gave BD intermediate 3, which was cyclized (low overall yield) to the D-homosteroid 4 [2,3]. The latter was identical with the product synthesized by an AB + D-+ABD-+ABCD route [4]. In an effort to obtain a 10-methyl homolog, 5 [5-7], was condensed with 2-methyl-,3-cyclohexanedione and the BD intermediate was cyclized to give 6 in moderate yield [6][7][8], All attempts to construct ring A onto 6, however, were unsuccessful [6,7].

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“…The first example of a steroid containing the indole ring system was synthesized from a BD intermediate [23]. Demethoxy 8 (Scheme 11-2) was converted via 28 and 29 into 30 (Scheme 11-5).…”

mentioning

confidence: 99%

“…Diazotization of 30 and reduction with stannous chloride gave the corresponding hydrazine in 57% yield; the latter was converted into 31 in 98% yield by reaction with ethyl pyruvate. Ring closure in alcoholic hydrogen chloride produced a 70% yield of 32, which was hydrolyzed and decarboxylated to afford a mixture from which 33 was isolated [23].…”

mentioning

confidence: 99%

B + D → Bd → BCD → Abcd

1974

Organic Chemistry: A Series of Monographs

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ChemInform Abstract: VOLLSYNTH. DES ERSTEN TYPS VON A,B‐INDOLOSTEROIDEN

Abstract: Als Ausgangsprodukt dient 3‐Phenyl‐2‐(carboxymethyl)‐2‐cyclopenten‐1‐on (I), aus dem über die Stufen (II)‐(VII) das tricyclische Amin (VIII) gewonnen wird.

Cited by 1 publication

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B + D → Bd → BCD → Abcd

B + D → Bd → BCD → Abcd

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