Abstract
A review on the biosynthetic and biomimetic electrocyclizations is presented that aims to provide a counterpart highlighting electrocyclic reactions that have been found or suspected in the biosynthesis of natural products. This review is organized beginning from the number of electrons involved in a given π system that undergoes the electrocyclic reaction, followed by electrocyclic reactions involving 6 and 8 π-electrons. Thermal and photochemical reactions are presented in the same order, while, systems that include heteroatoms which are confined to 6 π-electrons are presented separately. Finally, briefly addressed is the question of whether biosynthetic electrocyclizations require enzyme catalysis.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4757-4778 |
| Number of pages | 22 |
| Journal | Chemical Reviews |
| Volume | 105 |
| Issue number | 12 |
| DOIs | |
| State | Published - Dec 2005 |
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ASJC Scopus subject areas
- Chemistry(all)
Cite this
Biosynthetic and biomimetic electrocyclizations. / Beaudry, Christopher M.; Malerich, Jeremiah P.; Trauner, Dirk.
In: Chemical Reviews, Vol. 105, No. 12, 12.2005, p. 4757-4778.Research output: Contribution to journal › Review article
}
TY - JOUR
T1 - Biosynthetic and biomimetic electrocyclizations
AU - Beaudry, Christopher M.
AU - Malerich, Jeremiah P.
AU - Trauner, Dirk
PY - 2005/12
Y1 - 2005/12
N2 - A review on the biosynthetic and biomimetic electrocyclizations is presented that aims to provide a counterpart highlighting electrocyclic reactions that have been found or suspected in the biosynthesis of natural products. This review is organized beginning from the number of electrons involved in a given π system that undergoes the electrocyclic reaction, followed by electrocyclic reactions involving 6 and 8 π-electrons. Thermal and photochemical reactions are presented in the same order, while, systems that include heteroatoms which are confined to 6 π-electrons are presented separately. Finally, briefly addressed is the question of whether biosynthetic electrocyclizations require enzyme catalysis.
AB - A review on the biosynthetic and biomimetic electrocyclizations is presented that aims to provide a counterpart highlighting electrocyclic reactions that have been found or suspected in the biosynthesis of natural products. This review is organized beginning from the number of electrons involved in a given π system that undergoes the electrocyclic reaction, followed by electrocyclic reactions involving 6 and 8 π-electrons. Thermal and photochemical reactions are presented in the same order, while, systems that include heteroatoms which are confined to 6 π-electrons are presented separately. Finally, briefly addressed is the question of whether biosynthetic electrocyclizations require enzyme catalysis.
UR - http://www.scopus.com/inward/record.url?scp=30744456247&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=30744456247&partnerID=8YFLogxK
U2 - 10.1021/cr0406110
DO - 10.1021/cr0406110
M3 - Review article
C2 - 16351061
AN - SCOPUS:30744456247
VL - 105
SP - 4757
EP - 4778
JO - Chemical Reviews
JF - Chemical Reviews
SN - 0009-2665
IS - 12
ER -