Novel spiro-quinone formation from 3′-hydroxydiethylstilbestrol after oxidation with silver oxide

Muhammad Saeed; Eleanor Rogan; Ercole Cavalieri

doi:10.1016/j.tetlet.2005.04.131

Novel spiro-quinone formation from 3′-hydroxydiethylstilbestrol after oxidation with silver oxide

Muhammad Saeed, Eleanor Rogan, Ercole Cavalieri

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

The human carcinogen diethylstilbestrol (DES) is metabolized into 3′-hydroxydiethylstilbestrol (3′-OH-DES) (1). Chemical oxidation of the catechol metabolites with silver oxide in CH₂Cl₂ affords a novel spiro-quinone (3) in quantitative yield. Protection of the phenolic OH group followed by oxidation gives 4″-OCH₃-DES- 3′,4′-Q (5) in excellent yield.

Original language	English (US)
Pages (from-to)	4449-4451
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2005.04.131
State	Published - Jun 27 2005

Keywords

Catechol estrogen
Depurinating adducts
Diethylstilbestrol
Oxidation
spiro-Quinone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.04.131

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title = "Novel spiro-quinone formation from 3′-hydroxydiethylstilbestrol after oxidation with silver oxide",

abstract = "The human carcinogen diethylstilbestrol (DES) is metabolized into 3′-hydroxydiethylstilbestrol (3′-OH-DES) (1). Chemical oxidation of the catechol metabolites with silver oxide in CH2Cl2 affords a novel spiro-quinone (3) in quantitative yield. Protection of the phenolic OH group followed by oxidation gives 4″-OCH3-DES- 3′,4′-Q (5) in excellent yield.",

keywords = "Catechol estrogen, Depurinating adducts, Diethylstilbestrol, Oxidation, spiro-Quinone",

author = "Muhammad Saeed and Eleanor Rogan and Ercole Cavalieri",

note = "Funding Information: We thank Dr. P. Keifer, Eppley Institute, for helping to obtain 2-D NMR data. This research was supported by US Health Service Grant PO1 CA49210 from the National Cancer Institute. Core support in the Eppley Institute is provided by grant P30 CA36727 from the National Cancer Institute. ",

year = "2005",

month = jun,

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doi = "10.1016/j.tetlet.2005.04.131",

language = "English (US)",

volume = "46",

pages = "4449--4451",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

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T1 - Novel spiro-quinone formation from 3′-hydroxydiethylstilbestrol after oxidation with silver oxide

AU - Saeed, Muhammad

AU - Rogan, Eleanor

AU - Cavalieri, Ercole

N1 - Funding Information: We thank Dr. P. Keifer, Eppley Institute, for helping to obtain 2-D NMR data. This research was supported by US Health Service Grant PO1 CA49210 from the National Cancer Institute. Core support in the Eppley Institute is provided by grant P30 CA36727 from the National Cancer Institute.

PY - 2005/6/27

Y1 - 2005/6/27

N2 - The human carcinogen diethylstilbestrol (DES) is metabolized into 3′-hydroxydiethylstilbestrol (3′-OH-DES) (1). Chemical oxidation of the catechol metabolites with silver oxide in CH2Cl2 affords a novel spiro-quinone (3) in quantitative yield. Protection of the phenolic OH group followed by oxidation gives 4″-OCH3-DES- 3′,4′-Q (5) in excellent yield.

AB - The human carcinogen diethylstilbestrol (DES) is metabolized into 3′-hydroxydiethylstilbestrol (3′-OH-DES) (1). Chemical oxidation of the catechol metabolites with silver oxide in CH2Cl2 affords a novel spiro-quinone (3) in quantitative yield. Protection of the phenolic OH group followed by oxidation gives 4″-OCH3-DES- 3′,4′-Q (5) in excellent yield.

KW - Catechol estrogen

KW - Depurinating adducts

KW - Diethylstilbestrol

KW - Oxidation

KW - spiro-Quinone

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DO - 10.1016/j.tetlet.2005.04.131

M3 - Article

AN - SCOPUS:19544394051

SN - 0040-4039

VL - 46

SP - 4449

EP - 4451

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Novel spiro-quinone formation from 3′-hydroxydiethylstilbestrol after oxidation with silver oxide

Abstract

Keywords

ASJC Scopus subject areas

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