Synthesis of (11,11,12,12-2H4)progesterone for mass spectral investigations of peripheral metabolism

Journal Article · Tue May 01 00:00:00 EDT 1990 · Steroids; (USA)

DOI:https://doi.org/10.1016/0039-128X(90)90019-8· OSTI ID:6649405

Kirk, D N; Smith, C Z; Honour, J W ^[1]

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1. Queen Mary College, London (England)

Hecogenin has been transformed into (11,11,12,12-2H4)progesterone via base-catalyzed isotope exchange with D2O (at C-11), carbenic decomposition of the 12-tosylhydrazone formed by the use of (N,N,N'-2H3)toluene-p-sulfonylhydrazine, and reduction with (2H2)diimide to give (11,11,12,12-2H4)tigogenin, followed by standard degradation of the spiroketal side chain and dehydrogenation in ring A.

• OSTI ID: 6649405
• Journal Information: Steroids; (USA), Vol. 55:5; ISSN 0039-128X
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
PROGESTERONE
CHEMICAL PREPARATION
METABOLISM
DEUTERIUM
ISOTOPIC EXCHANGE
LABELLING
MASS SPECTRA
TRACER TECHNIQUES
HORMONES
HYDROGEN ISOTOPES
ISOTOPE APPLICATIONS
ISOTOPES
KETONES
LIGHT NUCLEI
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PREGNANES
SPECTRA
STABLE ISOTOPES
STEROID HORMONES
STEROIDS
SYNTHESIS
550501* - Metabolism- Tracer Techniques