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 journalArticlepeer-review

5 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 languageEnglish
Pages (from-to)12501-12508
Number of pages8
JournalChemistry - A European Journal
Volume21
Issue number35
DOIs
Publication statusPublished - 2015
Externally publishedYes

Keywords

  • crude oil
  • fossil biomarkers
  • natural products
  • steroids
  • structure elucidation

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