Investigation into 9(S)-HPODE-derived allene oxide to cyclopentenone cyclization mechanism via diradical oxyallyl intermediates-Reference-Cited by-同舟云学术

Investigation into 9(S)-HPODE-derived allene oxide to cyclopentenone cyclization mechanism via diradical oxyallyl intermediates

Published:2016 Issue:14 Volume:14 Page:3544-3557
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Hebert Sebastien P.¹²³⁴,Cha Jin K.¹²³⁴,Brash Alan R.⁵⁶⁷⁴,Schlegel H. Bernhard¹²³⁴

Affiliation:

1. Department of Chemistry

2. Wayne State University

3. Detroit

4. USA

5. Department of Pharmacology

6. Vanderbilt University

7. Nashville

Abstract

Calculations show that the open shell, diradical pathway is lower in energy than the closed shell reactions for Z- and E-allene oxide to cyclopropanone, and cyclopropanone to cyclopentenone.

Funder

National Institutes of Health

Division of Chemistry

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2016/OB/C6OB00204H

Reference53 articles.

1. Isolation and Characterization of Two Geometric Allene Oxide Isomers Synthesized from 9S-Hydroperoxylinoleic Acid by Cytochrome P450 CYP74C3

2. Cyclization of natural allene oxide fatty acids. The anchimeric assistance of β, γ -double bond beside the oxirane and the reaction mechanism

3. Formation of cyclopentenones from all-(E) hydroperoxides of linoleic acid via allene oxides. New insight into the mechanism of cyclization

4. Role of structure and pH in cyclization of allene oxide fatty acids: Implications for the reaction mechanism

5. Tomato CYP74C3 is a Multifunctional Enzyme not only Synthesizing Allene Oxide but also Catalyzing its Hydrolysis and Cyclization

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