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

Access to Document

10.1002/chem.201502148

Cite this

@article{7b17866b61e745faa0b99c6a651e4ccb,

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.",

keywords = "crude oil, fossil biomarkers, natural products, steroids, structure elucidation",

author = "Matthias Bender and Marc Schmidtmann and Summons, {Roger E.} and J{\"u}rgen Rullk{\"o}tter and Jens Christoffers",

year = "2015",

doi = "10.1002/chem.201502148",

language = "English",

volume = "21",

pages = "12501--12508",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH, Wiley",

number = "35",

}

TY - JOUR

T1 - A geomimetic approach to the formation and identification of fossil sterane biomarkers in crude oil

T2 - 18-nor-D-homo-androstane and 5α,14β-androstane

AU - Bender, Matthias

AU - Schmidtmann, Marc

AU - Summons, Roger E.

AU - Rullkötter, Jürgen

AU - Christoffers, Jens

PY - 2015

Y1 - 2015

N2 - 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.

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.

KW - crude oil

KW - fossil biomarkers

KW - natural products

KW - steroids

KW - structure elucidation

UR - http://www.scopus.com/inward/record.url?scp=84939466379&partnerID=8YFLogxK

U2 - 10.1002/chem.201502148

DO - 10.1002/chem.201502148

M3 - Article

C2 - 26239385

AN - SCOPUS:84939466379

SN - 0947-6539

VL - 21

SP - 12501

EP - 12508

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 35

ER -

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

Keywords

Access to Document

Other files and links

Fingerprint

Cite this