The Facile Synthesis of 19-Nortestosterone and 19-Norandrostenedione from Estrone

Wilds, A. L.; Nelson, Norman A.

doi:10.1021/ja01117a065

Cited by 133 publications

(24 citation statements)

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“…Palladium-catalyzed reduction of (165) forms (166). Treatment of (166) with pyridinium chlorochromate simultaneously oxidizes the C3-alcohol to a ketone, oxidizes the primary alcohol to an acid, eliminates the 5-hydroxy-3-ketone to an ene-one, and cyclizes the D-ring hydroxy acid to a lactone to form (167). Dehydrogenation of the C1-C2 bond with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) yields spirorenone (156) (184).…”

Section: Syntheses Several Improvements and Innovations Have Resultementioning

confidence: 99%

Steroids

Morgan¹,

Moynihan²

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Steroids are members of a large class of lipid compounds called terpenes that are biogenically derived from the same parent compound, isoprene, C 5 H 8 . Steroids contain or are derived from the perhydro‐1,2‐cyclopentenophenanthrene ring system and are found in a variety of different marine, terrestrial, and synthetic sources. Nonhormonal steroids, eg, sterols and bile acids; vitamin D; and hormonal steroids, eg, the human sex hormones (androgens, estrogens, and progestins) and corticosteroids (glucocorticoids and mineralocorticoids) play critical roles in the physiology and biochemistry of most living creatures. Other naturally occurring steroids, such as plant steroids, marine steroids, ecdysteroids, cardiac steroids, steroid alkaloids, and steroid antibiotics, have a plethora of biological activities and uses. Many synthetic steroids are the product of pharmaceutical research that has resulted in the development of several steroid‐based medicines with a market value over $10 billion. Among the medicinally important synthetic steroids, are antihormones, anesthetics, antiinflammatories, antiasthmatics, contraceptive drugs, antibiotics, anticancer agents, cardiovascular agents, and osteoporosis drugs.

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Section: Syntheses Several Improvements and Innovations Have Resultementioning

confidence: 99%

Steroids

Morgan¹,

Moynihan²

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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“…The first facile synthesis of 19-NA (nandrolone) was reported by Birch (1950) and confirmed by Wilds and Nelson (1953) with estrone as starting material. Since then, the pharmaceutical industry has produced norsteroids for human, and animal, substitutive (hypogonadism), complementary (osteoporosis and haemological diseases) or contraceptive treatment (Frankle and Leffers 1992;Mauvais-Jarvis 1984;Schu¨rmeyer et al 1984;Segaloff 1963;Wilson 1988).…”

Section: Origin Of Endogenous Nandrolone and Norsteroidsmentioning

confidence: 96%

Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances?

Bricout

Wright

2004

European Journal of Applied Physiology

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Norsteroids are xenobiotics with androgenic and anabolic properties known since as far back as the 1930s. In doping controls, the use of the banned xenobiotic norsteroids is detected in the competitor's urines by the measurement of norandrosterone (19-NA) and noretiocholanolone (19-NE), which are the main metabolites for nandrolone (NT) and most norsteroids with anabolic properties. In 1996, the IOC subcommission "Doping and Biochemistry of Sport" informed the Heads of the "IOC Accredited Laboratories" that the recommended cut-off limit for reporting an offence was to be 1-2 ng ml(-1) urine for either 19-NA or 19-NE. We will discuss how technical progress in gas chromatography coupled to high-resolution mass spectrometry permitted a dramatic increase in sensitivity with a detection limit of 1 pg ml(-1) urine, or less, and an assay limit of 20-50 pg ml(-1) urine, for either 19-NA or 19-NE. As a paradox, norsteroids have been known for decades as not only xenobiotics but also obligatory endogenous intermediates in the biosynthesis of estrogens from androgens in all species, man included. It is this biochemical observation which fed the active scientific and medical controversy initiated in 1998 over the possibly endogenous production of nandrolone and metabolites well over the new IOC's recommended cut-off limit of 2 ng ml(-1) urine. Notwithstanding the particular technical difficulties attached, we will provide data and discuss the minute endogenous levels detected and measured in man either at rest, after performance or training and compare them to the relatively high levels reported in male athlete's doping controls today. We will also discuss data on the pharmacological effects of some contraceptive therapies containing norsteroids in women. In view of the well-documented noxious effects repeatedly observed after anabolic steroid misuse, the confirmation and implementation of technically proven procedures for reporting norsteroid abuse in sports seems an important enough goal to protect athlete's health against such abuses and justifies up dating the review of the patent scientific and medical experience and knowledge gained over the last 50 years on nandrolone and its minor production in man and woman.

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“…Use of the Birch reduction for synthesis of 19-norsteroids is well known outside the area of total synthesis as a result initially of the pioneering work of Birch [109] and of refinements by Wilds [110]; it has been applied to both A and D rings in the total synthesis of steroids. Birch reduction of 136 (Scheme 1-13), followed by hydrolysis gave the unsaturated ketone 137 [111].…”

Section: Reduction Of Aromatic Rings Metal-ammonia Reductionsmentioning

confidence: 99%

Designing Total Syntheses

1974

Organic Chemistry: A Series of Monographs

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The Facile Synthesis of 19-Nortestosterone and 19-Norandrostenedione from Estrone

Cited by 133 publications

References 3 publications

Steroids

Steroids

Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances?

Designing Total Syntheses

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