A geomimetic approach to the formation and identification of fossil sterane biomarkers in crude oil: 18-nor-D-homo-androstane and 5α,14β-androstane

Matthias Bender; Marc Schmidtmann; Roger E. Summons; Jürgen Rullkötter; Jens Christoffers

doi:10.1002/chem.201502148

A geomimetic approach to the formation and identification of fossil sterane biomarkers in crude oil: 18-nor-D-homo-androstane and 5α,14β-androstane

Matthias Bender, Marc Schmidtmann, Roger E. Summons, Jürgen Rullkötter, Jens Christoffers^*

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

A diazonium ion derived from 18-aminoandrostane rearranged upon decomposition by a carbonium and a carbenium ion to furnish a mixture of a cyclopropanated compound and two D-homo-androstenes. Hydrogenation of this mixture gave the saturated hydrocarbons, 18-nor-D-homo-androstane and 5α,14β-androstane, which are both fossil sterane biomarkers in Neoproterozoic crude oil. The so far unknown constitution and configuration as well as the geochemical genesis were established by this experiment. The starting material for this investigation, 18-aminoandrostane, was prepared in twelve steps from androstan-17-one (12.5% overall yield) with a Barton reaction as the key step.

Original language	English
Pages (from-to)	12501-12508
Number of pages	8
Journal	Chemistry - A European Journal
Volume	21
Issue number	35
DOIs	https://doi.org/10.1002/chem.201502148
Publication status	Published - 2015
Externally published	Yes

Keywords

crude oil
fossil biomarkers
natural products
steroids
structure elucidation

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10.1002/chem.201502148

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title = "A geomimetic approach to the formation and identification of fossil sterane biomarkers in crude oil: 18-nor-D-homo-androstane and 5α,14β-androstane",

abstract = "A diazonium ion derived from 18-aminoandrostane rearranged upon decomposition by a carbonium and a carbenium ion to furnish a mixture of a cyclopropanated compound and two D-homo-androstenes. Hydrogenation of this mixture gave the saturated hydrocarbons, 18-nor-D-homo-androstane and 5α,14β-androstane, which are both fossil sterane biomarkers in Neoproterozoic crude oil. The so far unknown constitution and configuration as well as the geochemical genesis were established by this experiment. The starting material for this investigation, 18-aminoandrostane, was prepared in twelve steps from androstan-17-one (12.5\% overall yield) with a Barton reaction as the key step.",

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AU - Schmidtmann, Marc

AU - Summons, Roger E.

AU - Rullkötter, Jürgen

AU - Christoffers, Jens

PY - 2015

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AB - A diazonium ion derived from 18-aminoandrostane rearranged upon decomposition by a carbonium and a carbenium ion to furnish a mixture of a cyclopropanated compound and two D-homo-androstenes. Hydrogenation of this mixture gave the saturated hydrocarbons, 18-nor-D-homo-androstane and 5α,14β-androstane, which are both fossil sterane biomarkers in Neoproterozoic crude oil. The so far unknown constitution and configuration as well as the geochemical genesis were established by this experiment. The starting material for this investigation, 18-aminoandrostane, was prepared in twelve steps from androstan-17-one (12.5% overall yield) with a Barton reaction as the key step.

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KW - fossil biomarkers

KW - natural products

KW - steroids

KW - structure elucidation

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A geomimetic approach to the formation and identification of fossil sterane biomarkers in crude oil: 18-nor-D-homo-androstane and 5α,14β-androstane

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Keywords

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