Dehydrierung von Steroiden, XIII. Bildung dehydrierter Steroid‐Chloranil‐Dienadditionsverbindungen

Dannenberg, Heinz; Hebenbrock, Klaus-Friedrich

doi:10.1002/jlac.19667000114

Justus Liebigs Ann. Chem.

1966

DOI: 10.1002/jlac.19667000114

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Dehydrierung von Steroiden, XIII. Bildung dehydrierter Steroid‐Chloranil‐Dienadditionsverbindungen

Heinz Dannenberg

Klaus-Friedrich Hebenbrock

Abstract: Die Dehydrierung von 7-Dehydro-cholesterin (1: R = CsH17) und von Ergosterin (1: R = C9H17) mit Chloranil fuhrt, auBer zu bereits bekannten Dehydrierungsprodukten von Steroiden

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2004

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“…Thus, the structure of compound 1 was established as (17β,20 R ,22 E ,24 R )-19-norergosta-1,3,5,7,9,14,22-heptaene. This compound was synthesized previously …”

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Natural Aromatic Steroids as Potential Molecular Fossils from the Fruiting Bodies of the Ascomycete Daldinia concentrica

Qin

Liu

2004

J. Nat. Prod.

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The identification of aromatic steroid hydrocarbons bearing a methyl group at positions 1, 2, 3, 4, or 6 in sediments and petroleum has been puzzling since possible steroidal precursors have not yet been reported in living organisms. Two new aromatic steroids, (17beta,20R,22E,24R)-19-norergosta-1,3,5,7,9,14,22-heptaene (1) and (17beta,20R,22E,24R)-1-methyl-19-norergosta-1,3,5,7,9,14,22-heptaene (2), were isolated from the ascomycete Daldinia concentrica, of which compound 2 bears an unusual methyl group at position 1. We propose that the origin of these compounds is derived from the transformation undergone by their precursor due to microbial action. Compounds 1 and 2 could be the long-sought, biological precursor steroids for organic matter in Earth's subsurface.

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“…Thus, the structure of compound 1 was established as (17β,20 R ,22 E ,24 R )-19-norergosta-1,3,5,7,9,14,22-heptaene. This compound was synthesized previously …”

mentioning

confidence: 99%

“…This compound was synthesized previously. 28 Compound 2 was obtained as pale green needles. The EIMS gave a molecular ion peak at m/z 372.…”

mentioning

confidence: 99%

Natural Aromatic Steroids as Potential Molecular Fossils from the Fruiting Bodies of the Ascomycete Daldinia concentrica

Qin

Liu

2004

J. Nat. Prod.

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Dehydrierung von Steroiden, XIII. Bildung dehydrierter Steroid‐Chloranil‐Dienadditionsverbindungen

Abstract: Die Dehydrierung von 7-Dehydro-cholesterin (1: R = CsH17) und von Ergosterin (1: R = C9H17) mit Chloranil fuhrt, auBer zu bereits bekannten Dehydrierungsprodukten von Steroiden

Cited by 1 publication

References 8 publications

Natural Aromatic Steroids as Potential Molecular Fossils from the Fruiting Bodies of the Ascomycete Daldinia concentrica

Natural Aromatic Steroids as Potential Molecular Fossils from the Fruiting Bodies of the Ascomycete Daldinia concentrica

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