Biosynthetic and biomimetic electrocyclizations

Christopher M. Beaudry, Jeremiah P. Malerich, Dirk Trauner

Research output: Contribution to journalReview article

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 languageEnglish (US)
Pages (from-to)4757-4778
Number of pages22
JournalChemical Reviews
Volume105
Issue number12
DOIs
StatePublished - Dec 2005

Fingerprint

Biomimetics
Electrons
Photochemical reactions
Biosynthesis
Biological Products
Catalysis
Enzymes

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Beaudry, C. M., Malerich, J. P., & Trauner, D. (2005). Biosynthetic and biomimetic electrocyclizations. Chemical Reviews, 105(12), 4757-4778. https://doi.org/10.1021/cr0406110

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 journalReview article

Beaudry, CM, Malerich, JP & Trauner, D 2005, 'Biosynthetic and biomimetic electrocyclizations', Chemical Reviews, vol. 105, no. 12, pp. 4757-4778. https://doi.org/10.1021/cr0406110
Beaudry CM, Malerich JP, Trauner D. Biosynthetic and biomimetic electrocyclizations. Chemical Reviews. 2005 Dec;105(12):4757-4778. https://doi.org/10.1021/cr0406110
Beaudry, Christopher M. ; Malerich, Jeremiah P. ; Trauner, Dirk. / Biosynthetic and biomimetic electrocyclizations. In: Chemical Reviews. 2005 ; Vol. 105, No. 12. pp. 4757-4778.
@article{4086995b587f48d4ba28b1ea06d787a3,
title = "Biosynthetic and biomimetic electrocyclizations",
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.",
author = "Beaudry, {Christopher M.} and Malerich, {Jeremiah P.} and Dirk Trauner",
year = "2005",
month = "12",
doi = "10.1021/cr0406110",
language = "English (US)",
volume = "105",
pages = "4757--4778",
journal = "Chemical Reviews",
issn = "0009-2665",
publisher = "American Chemical Society",
number = "12",

}

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 -