Synthesis of new pentacyclic heterocyclic steroidal analogs, 6-oxabenz[3,4]-d-homoestra- 1,3,5(10),8,14-pentaen-17α-one and 3a,4,5,13-tetrahydro-3H- [2]benzothieno[5,4-d]naphtho- [1,2-b]pyran☆
TL;DR: The total synthesis of new pentacyclic heterocyclic steroidal analogs, 6-oxabenz[3,4], 1,3,5(10),8,14-pentaen-17a-one and 3a,4,5,13-tetrahydro-3H-[2]benzothieno[5,4-d]naphtho[1,2-b]-pyran is described.
Abstract: Total synthesis of new pentacyclic heterocyclic steroidal analogs, 6-oxabenz[3,4]- d -homoestra 1,3,5(10),8,14-pentaen-17a-one and 3a,4,5,13-tetrahydro-3H-[2]benzothieno[5,4-d]naphtho[1,2-b]-pyran, from 4-oxa-1,2,3,4-tetrahydrophenanthren-I-one is described.
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TL;DR: The continuous interest in the field of oxasteroids mainly arises from the fascinating aspects associated with their peculiar stereochemical features and their promising and sometimes unexpected biological activities.
Abstract: The continuous interest in the field of oxasteroids mainly arises from the fascinating aspects associated with their peculiar stereochemical features and their promising and sometimes unexpected biological activities. The recent development in the partial and total syntheses of oxasteroids are herein described.
41 citations
TL;DR: A review of literature on the synthesis of pentacyclic steroids is presented and it is shown that the steroids are among the most important secondary metabolites.
Abstract: Due to their high profile biological activity, the steroids are among the most important secondary metabolites. A review of literature on the synthesis of pentacyclic steroids is presented.
28 citations
Cites background from "Synthesis of new pentacyclic hetero..."
...In 1991, the same authors [22] described the total synthesis of new pentacyclic heterocyclic steroidal analogs, 6oxabenz[3,4]-d-homoestra-1,3,5(10),8,14-pentaen-17a-one 30 and 3a,4,5,13-tetrahydro-3H-[2]benzothieno[5,4-d]naphto[1,2b]pyran 32, from 4-oxa-1,2,3,4-tetrahydrophenanthren-1-one (Scheme 7)....
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TL;DR: In this paper, total synthesis of tetracyclic heterogonane ring systems was achieved from 1-oxo-4-thia-1,2,3,4-tetrahydrophenanthrene and its oxa analogue.
Abstract: Total synthesis of tetracyclic heterogonane ring systems(1,2 & 3) were achieved from 1-oxo-4-thia-1,2,3,4-tetrahydrophenanthrene(4) and its oxa analogue(5)
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66 citations
TL;DR: Synthese du compose du titre a partir de l'oxo-3acetoxy-5cyclopentenedicarboxylate-1,2 de dimethyle via un cetoester chiral utilise dans la synthese de PGF 2 α(+).
Abstract: Synthese du compose du titre a partir de l'oxo-3acetoxy-5cyclopentenedicarboxylate-1,2 de dimethyle via un cetoester chiral utilise dans la synthese de PGF 2 α(+)
44 citations
TL;DR: In this article, the effects of (±)-13β, 17α-diethyl-17β-hydroxygon-4-en-3-one were compared with resolved samples of the component enantiomers.
Abstract: Various biological effects of (±)-13β-ethyl-17β-hydroxygon-4-en-3-one, (±)-13β-ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-one, and (±)-13β, 17α-diethyl-17β-hydroxygon-4-en-3-one were compared with resolved samples of the component enantiomers. The data were commensurate with the hypothesis that biological activity resides in the enantiomers possessing absolute configurations corresponding to those of the natural steroid hormones.
36 citations
TL;DR: Es wird über die Totalsynthese von verschiedenen Derivaten des (±)-6-Oxa- und Aza-Östrons und die Umwandlung von (±-17β-Oxy-3-methoxy-6-oxa-östratrien-1, 3, 510 zu Verbindungen der (±)19-Nor-6
Abstract: Es wird uber die Totalsynthese von verschiedenen Derivaten des (±)-6-Oxa- und Aza-Ostrons und die Umwandlung von (±)-17β-Oxy-3-methoxy-6-oxa-ostratrien-1, 3, 510 zu Verbindungen der (±)-19-Nor-6-oxa-testosteron-Klasse berichtet. Die biologische Wirksamkeit der Glieder in der 6-Oxa-Reihe wird beschrieben.
23 citations
TL;DR: The total synthesis of a series of racemic C-18 functionalized steroids was carried out in a search for novel estrogen-and/or progestin-receptor agonists or antagonists, which showed little activity in the Clauberg and anti-Clauberg assays.
Abstract: The total synthesis of a series of racemic C-18 functionalized steroids was carried out in a search for novel estrogen-and/or progestin-receptor agonists or antagonists. The target compound 3,18-dihydroxyestra-1,3,5(10)-triene (2), 13-(2-oxopropyl)gona-4-en-3-one (3), 13-(1-hydroxy-1-prop-2-ynyl)gona-4-en-3-one (4a and 4b) and 13-(1-acetoxy-2-oxo-1-propyl)gona-4-en-3-one (5) are position isomers of the highly biologically active estradiol, progesterone, norethindrone, and 17-acetoxyprogesterone, respectively. Nevertheless the synthetic C-18 functionalized steroids 3-5 showed little activity in the Clauberg and anti-Clauberg assays. Compound 2 showed no antagonism in the postcoital assay despite the fact that it exhibited weak but measurable in vitro receptor-binding activity.
18 citations