Literature DB >> 17257636

A facile total synthesis of ent-17beta-estradiol and structurally related analogues.

Zu Yun Cai1, Douglas F Covey.   

Abstract

A facile six-step synthesis (15.2% yield) of ent-17beta-estradiol from readily accessible precursors is described. The preparation of analogues with 2-alkyl substituents, double bond unsaturation in the C-ring, a cis C,D-ring fusion and modified substituents at C(17) is also reported.

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Year:  2006        PMID： 17257636      PMCID： PMC3791855          DOI： 10.1016/j.steroids.2006.12.007

Source DB:  PubMed          Journal:  Steroids        ISSN： 0039-128X            Impact factor:   2.668


  16 in total

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Journal:  J Org Chem       Date:  1975-03-21       Impact factor: 4.354

2.  Neuroprotection against oxidative stress by estrogens: structure-activity relationship.

Authors:  C Behl; T Skutella; F Lezoualc'h; A Post; M Widmann; C J Newton; F Holsboer
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3.  Differential inhibition in vitro of 17 beta-estradiol binding in the mouse uterus and vagina by optical antipodes of estrogens.

Authors:  L Terenius
Journal:  Mol Pharmacol       Date:  1968-07       Impact factor: 4.436

4.  Total synthesis of natural and non-natural steroid hormones.

Authors:  U Eder
Journal:  J Steroid Biochem       Date:  1979-07       Impact factor: 4.292

5.  Phenolic A ring requirement for the neuroprotective effects of steroids.

Authors:  P S Green; K Gordon; J W Simpkins
Journal:  J Steroid Biochem Mol Biol       Date:  1997 Nov-Dec       Impact factor: 4.292

6.  The nonfeminizing enantiomer of 17beta-estradiol exerts protective effects in neuronal cultures and a rat model of cerebral ischemia.

Authors:  P S Green; S H Yang; K R Nilsson; A S Kumar; D F Covey; J W Simpkins
Journal:  Endocrinology       Date:  2001-01       Impact factor: 4.736

7.  Novel "scavestrogens" and their radical scavenging effects, iron-chelating, and total antioxidative activities: delta 8,9-dehydro derivatives of 17 alpha-estradiol and 17 beta-estradiol.

Authors:  W Römer; M Oettel; P Droescher; S Schwarz
Journal:  Steroids       Date:  1997-03       Impact factor: 2.668

8.  Totally synthetic steroid hormones. 13. The chemical resolution of some racemic estrane, 13-beta-ethylgonane, and 13-beta-n-propylgonane derivatives and the preparation of some estrane and 13-beta-ethylgonane derivatives of unnatural configuration.

Authors:  G C Buzby; D Hartley; G A Hughes; H Smith; B W Gadsby; A B Jansen
Journal:  J Med Chem       Date:  1967-03       Impact factor: 7.446

9.  Superior and distinct antioxidant effects of selected estrogen metabolites on lipid peroxidation.

Authors:  M Tang; W Abplanalp; S Ayres; M T Subbiah
Journal:  Metabolism       Date:  1996-04       Impact factor: 8.694

10.  Synthesis of new 16-spirosteroids.

Authors:  L F Tietze; J Wölfling; G Schneider; M Noltemeyer
Journal:  Steroids       Date:  1994-05       Impact factor: 2.668
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  2 in total

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Journal:  ACS Chem Neurosci       Date:  2018-06-05       Impact factor: 4.418

Review 2.  Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules.

Authors:  Thilo Focken; Stephen Hanessian
Journal:  Beilstein J Org Chem       Date:  2014-08-13       Impact factor: 2.883
  2 in total

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