Asymmetric and Symmetric Total Synthesis

A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: closed (31 October 2022) | Viewed by 4228

Special Issue Editors


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Guest Editor
1. University of Michigan Library, University of Michigan, 3162 Shapiro, 919 South University Avenue, Ann Arbor, MI 48109-1185, USA
2. The Michigan Institute for Data Science, University of Michigan, Weiser Hall, 500 Church Street, Suite 600, Ann Arbor, MI 48109-1042, USA

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Guest Editor
Toyota Research Institute of North America, 1555 Woodridge Avenue, Ann Arbor, MI 48105, USA

Special Issue Information

Dear Colleagues,

Total synthesis of natural products stands as one of the most daunting fields of chemical synthesis. Behind the novelty and beauty of intricate three-dimensional architectures of secondary metabolites lie many challenges that require exquisite precision in the selected synthetic strategies, turning total synthesis into a fine and very demanding art. Among the vast list of synthetic strategies available, those exploiting molecular symmetry can be very powerful and effective and significantly simplify the construction of apparently complex molecular frameworks.

The aim of the present Special Issue on “Asymmetric and Symmetric Total Synthesis” is to emphasize the role of symmetry in natural product synthesis, such as synthesis of symmetric molecules, symmetric strategies to construct molecules or desymmetrization strategies. We invite manuscripts covering a broad range of topics, including (though not limited to) the following:

- Desymmetrization of meso compounds in total synthesis of natural products;

- Catalytic enzymatic processes that involve desymmetrization;

- Total synthesis of highly symmetric natural products;

- Asymmetric total synthesis of highly symmetric products;

- Strategic use of limited molecular symmetry in natural products synthesis either through desymmetrization or by sharing a common fragment.

Dr. Yulia V. Sevryugina
Dr. Oscar Tutusaus
Guest Editors

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. Symmetry is an international peer-reviewed open access monthly 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 2400 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.

Published Papers (2 papers)

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Research

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9 pages, 3187 KiB  
Article
Synthesis and Evaluation of C2-Symmetric SPIROL-Based bis-Oxazoline Ligands
by Siyuan Sun, Nicolas A. Diaz and Pavel Nagorny
Symmetry 2021, 13(9), 1667; https://doi.org/10.3390/sym13091667 - 09 Sep 2021
Viewed by 1649
Abstract
This communication describes the synthesis of new bis-oxazoline chiral ligands (SPIROX) derived from the C2-symmetric spirocyclic scaffold (SPIROL). The readily available (R,R,R)-SPIROL (2) previously developed by our group was subjected to a three-step sequence that provided key diacid intermediate ( [...] Read more.
This communication describes the synthesis of new bis-oxazoline chiral ligands (SPIROX) derived from the C2-symmetric spirocyclic scaffold (SPIROL). The readily available (R,R,R)-SPIROL (2) previously developed by our group was subjected to a three-step sequence that provided key diacid intermediate (R,R,R)-7 in 75% yield. This intermediate was subsequently coupled with (R)- and (S)-phenylglycinols to provide diastereomeric products, the cyclization of which led to two diastereomeric SPIROX ligands (R,R,R,R,R)-3a and (R,R,R,S,S)-3b in 85% and 79% yield, respectively. The complexation of (R,R,R,R,R)-3a and (R,R,R,S,S)-3b with CuCl and Cu(OTf)2 resulted in active catalysts that promoted the asymmetric reaction of α-diazopropionate and phenol. The resultant O–H insertion product was formed in 88% yield, and with excellent selectivity (97% ee) when ligand (R,R,R,R,R)-3a was used. Full article
(This article belongs to the Special Issue Asymmetric and Symmetric Total Synthesis)
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Review

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14 pages, 2842 KiB  
Review
Non-Enzymatic Desymmetrization Reactions in Aqueous Media
by Satomi Niwayama
Symmetry 2021, 13(4), 720; https://doi.org/10.3390/sym13040720 - 19 Apr 2021
Cited by 3 | Viewed by 1763
Abstract
Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the [...] Read more.
Symmetric organic compounds are generally obtained inexpensively, and therefore they can be attractive building blocks for the total synthesis of various pharmaceuticals and natural products. The drawback is that discriminating the identical functional groups in the symmetric compounds is difficult. Water is the most environmentally benign and inexpensive solvent. However, successful organic reactions in water are rather limited due to the hydrophobicity of organic compounds in general. Therefore, desymmetrization reactions in aqueous media are expected to offer versatile strategies for the synthesis of a variety of significant organic compounds. This review focuses on the recent progress of desymmetrization reactions of symmetric organic compounds in aqueous media without utilizing enzymes. Full article
(This article belongs to the Special Issue Asymmetric and Symmetric Total Synthesis)
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