Synthesis of Biological Markers in Fossil Fuels. 4.1 C27, C28, and C29 13β, 17α(H)-Diasteranes

Phillip E. Bauer; David A. Nelson; David S. Watt; Joseph H. Reibenspies; Oren P. Anderson; Wolfgang K. Seifert; J. Michael Moldowan

doi:10.1021/jo00350a003

Synthesis of Biological Markers in Fossil Fuels. 4.¹ C₂₇, C₂₈, and C₂₉ 13β, 17α(H)-Diasteranes

Phillip E. Bauer
, David A. Nelson
, David S. Watt
, Joseph H. Reibenspies
, Oren P. Anderson
, Wolfgang K. Seifert
, J. Michael Moldowan

Molecular and Cellular Biochemistry

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

16 Scopus citations

Abstract

The rearrangement of 5-cholestene to (20ξ)-13(17)-diacholestenes, separation of C-20 epimers, and further reduction provided an unambiguous synthesis of the biomarkers (20R)- and (20S)-13β, 17α(H)-diacholestanes. Repetition of this sequence using (24R)-5-campestene or (24R)-5-stigmastene provided the analogous C₂₈ and C₂₉ diasteranes.

Original language	English
Pages (from-to)	5460-5464
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	50
Issue number	26
DOIs	https://doi.org/10.1021/jo00350a003
State	Published - Dec 1985

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Organic Chemistry

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title = "Synthesis of Biological Markers in Fossil Fuels. 4.1 C27, C28, and C29 13β, 17α(H)-Diasteranes",

abstract = "The rearrangement of 5-cholestene to (20ξ)-13(17)-diacholestenes, separation of C-20 epimers, and further reduction provided an unambiguous synthesis of the biomarkers (20R)- and (20S)-13β, 17α(H)-diacholestanes. Repetition of this sequence using (24R)-5-campestene or (24R)-5-stigmastene provided the analogous C28 and C29 diasteranes.",

author = "Bauer, \{Phillip E.\} and Nelson, \{David A.\} and Watt, \{David S.\} and Reibenspies, \{Joseph H.\} and Anderson, \{Oren P.\} and Seifert, \{Wolfgang K.\} and Moldowan, \{J. Michael\}",

year = "1985",

month = dec,

doi = "10.1021/jo00350a003",

language = "English",

volume = "50",

pages = "5460--5464",

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T1 - Synthesis of Biological Markers in Fossil Fuels. 4.1 C27, C28, and C29 13β, 17α(H)-Diasteranes

AU - Bauer, Phillip E.

AU - Nelson, David A.

AU - Watt, David S.

AU - Reibenspies, Joseph H.

AU - Anderson, Oren P.

AU - Seifert, Wolfgang K.

AU - Moldowan, J. Michael

PY - 1985/12

Y1 - 1985/12

N2 - The rearrangement of 5-cholestene to (20ξ)-13(17)-diacholestenes, separation of C-20 epimers, and further reduction provided an unambiguous synthesis of the biomarkers (20R)- and (20S)-13β, 17α(H)-diacholestanes. Repetition of this sequence using (24R)-5-campestene or (24R)-5-stigmastene provided the analogous C28 and C29 diasteranes.

AB - The rearrangement of 5-cholestene to (20ξ)-13(17)-diacholestenes, separation of C-20 epimers, and further reduction provided an unambiguous synthesis of the biomarkers (20R)- and (20S)-13β, 17α(H)-diacholestanes. Repetition of this sequence using (24R)-5-campestene or (24R)-5-stigmastene provided the analogous C28 and C29 diasteranes.

UR - https://www.scopus.com/pages/publications/0345100436

UR - https://www.scopus.com/pages/publications/0345100436#tab=citedBy

U2 - 10.1021/jo00350a003

DO - 10.1021/jo00350a003

M3 - Article

AN - SCOPUS:0345100436

SN - 0022-3263

VL - 50

SP - 5460

EP - 5464

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

Synthesis of Biological Markers in Fossil Fuels. 4.¹ C₂₇, C₂₈, and C₂₉ 13β, 17α(H)-Diasteranes

Abstract

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