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Organics
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Pericyclic Reactions in Organic Synthesis
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Pericyclic Reactions in Organic Synthesis

A special issue of Organics (ISSN 2673-401X).

Deadline for manuscript submissions: closed (31 July 2021) | Viewed by 12215

Special Issue Editor

Prof. Dr. Stéphane P. Roche

E-Mail Website
Guest Editor
Department of Chemistry and Biochemistry, Florida Atlantic University (FAU), 777 Glades Road, Boca Raton, FL 33431, USA
Interests: synthetic organic chemistry; reaction design; natural product synthesis; biomimetic synthesis; chemical biology; drug discovery

Special Issue Information

Dear Colleagues,

Within the realm of natural product synthesis, pericyclic reactions have played a pivotal role in discovering a new path to constructing and rearranging medium-sized carbocyclic scaffolds. Over time, a variety of pericyclic reactions (e.g. cycloadditions, sigmatropic reactions, electrocyclic and ene reactions) have been evaluated, to optimize the efficiency of synthetic routes in assembling complex small molecules and natural products. The significant chemo-, regio-, and stereo-control achievable by these reactions, as well as their efficiency in forming a number of hindered C-C bonds in a single step, the atom economy, and the minimal waste produced are of paramount importance for the synthetic chemists of the 21st century, in terms of synthesizing novel molecules and ever larger chemical libraries for drug-led screening.

This issue intends to highlight some of the most important discoveries and recent mechanistic considerations in pericyclic reactions that have fuelled, and will continue to fuel, our understanding, and translate into chemical efficiency.

Prof. Dr. Stéphane P. Roche
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Organics is an international peer-reviewed open access quarterly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1000 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Sigmatropic reactions
  • Cycloadditions
  • Electrocyclic reactions
  • Ene reactions
  • Mechamnistic considerations in pericyclic reactions

Published Papers (3 papers)

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Research

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7 pages, 2027 KiB  
Communication
Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes
by Takahiro Suzuki, Riko Nagahama, Muhammad Aiman Fariz, Yuki Yukutake, Kazutada Ikeuchi and Keiji Tanino
Organics 2021, 2(3), 306-312; https://0-doi-org.brum.beds.ac.uk/10.3390/org2030016 - 02 Sep 2021
Cited by 5 | Viewed by 3658
Abstract
Illisimonin A is a new sesquiterpene isolated from Illicium simonsii, and it possesses a novel 5/5/5/5/5 pentacyclic skeleton. The tricyclic skeleton of illisimonin A, tricyclo[5.2.1.01,5]decane, is presumed to be biosynthesized from allo-cedranes via a skeletal rearrangement. Herein, we report [...] Read more.
Illisimonin A is a new sesquiterpene isolated from Illicium simonsii, and it possesses a novel 5/5/5/5/5 pentacyclic skeleton. The tricyclic skeleton of illisimonin A, tricyclo[5.2.1.01,5]decane, is presumed to be biosynthesized from allo-cedranes via a skeletal rearrangement. Herein, we report the concise synthesis of highly oxidized allo-cedranes by an intramolecular Diels–Alder reaction using ortho-benzoquinones and demonstrate the biomimetic transformation of allo-cedranes by a retro-Claisen/aldol pathway. Full article
(This article belongs to the Special Issue Pericyclic Reactions in Organic Synthesis)
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Review

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12 pages, 2419 KiB  
Review
Recent Advances in Oxa-6π Electrocyclization Reactivity for the Synthesis of Privileged Natural Product Scaffolds
by Stéphane P. Roche
Organics 2021, 2(4), 376-387; https://0-doi-org.brum.beds.ac.uk/10.3390/org2040021 - 26 Oct 2021
Cited by 5 | Viewed by 3721
Abstract
The stunning advances in understanding the reactivity and selectivity principles of asymmetric pericyclic reactions have had a profound impact on the synthetic planning of complex natural products. Indeed, electrocyclizations, cycloadditions, and sigmatropic rearrangements enable synthetic chemists to craft highly functionalized scaffolds that would [...] Read more.
The stunning advances in understanding the reactivity and selectivity principles of asymmetric pericyclic reactions have had a profound impact on the synthetic planning of complex natural products. Indeed, electrocyclizations, cycloadditions, and sigmatropic rearrangements enable synthetic chemists to craft highly functionalized scaffolds that would not otherwise be possible with a similar atom-, step-, and redox-economy. In this review, selected examples from the last two decades of research (2003–2020) on tandem processes combining oxa-6π electrocyclic reactions are discussed in terms of reactivity challenges, inherent reversibility, and key structural bond formation in the assembly of natural products. A particular emphasis is given to the electrocyclic ring-closures in the tandem processes featuring Knoevenagel-type condensations, Diels–Alder cycloadditions, Stille couplings, and oxidative dearomatizations. The synthetic manifolds reviewed here illustrate how oxa-6π electrocyclizations are intimately linked to the construction of complex natural product scaffolds and have inspired a number of biomimetic syntheses in the laboratory. Full article
(This article belongs to the Special Issue Pericyclic Reactions in Organic Synthesis)
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Scheme 1

25 pages, 31428 KiB  
Review
Electrocyclizations of Conjugated Azapolyenes Produced in Reactions of Azaheterocycles with Metal Carbenes
by Nikolai V. Rostovskii, Mikhail S. Novikov and Alexander F. Khlebnikov
Organics 2021, 2(3), 313-336; https://0-doi-org.brum.beds.ac.uk/10.3390/org2030017 - 14 Sep 2021
Cited by 2 | Viewed by 3141
Abstract
Conjugated azapolyenes (azabuta-1,3-dienes, aza-/diaza-/oxaza-/oxadiazahexa-1,3,5-trienes) are highly reactive in electrocyclization reactions, which makes them convenient precursors for the synthesis of a wide range of four-, five-, and six-membered nitrogen heterocycles that are of relevance for medicinal chemistry. Ring opening reactions of 2H-azirines [...] Read more.
Conjugated azapolyenes (azabuta-1,3-dienes, aza-/diaza-/oxaza-/oxadiazahexa-1,3,5-trienes) are highly reactive in electrocyclization reactions, which makes them convenient precursors for the synthesis of a wide range of four-, five-, and six-membered nitrogen heterocycles that are of relevance for medicinal chemistry. Ring opening reactions of 2H-azirines and azoles containing an N–N or N–O bond, initiated by a transition metal carbene, have become increasingly important in recent years, since they easily allow the generation of azapolyenes with different numbers of double bonds and heteroatoms in various positions. This review summarizes the literature, published mainly in the last decade, on the synthetic and mechanistic aspects of electrocyclizations of azapolyenes generated by the carbene method. Full article
(This article belongs to the Special Issue Pericyclic Reactions in Organic Synthesis)
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