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Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress.
Molecules. 2022 Jun 02; 27(11)M

Abstract

With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and heterocycles from readily available unsaturated molecular building blocks, with increased selectivity, atom economy, sustainability and product diversity. In this review, synthetic methods for creating cyclic fragrances, including both natural and synthetic ones, will be discussed, with a focus on the key transformations of alkenes, alkynes, dienes and enynes. Several strategies will be discussed, including cycloaddition, catalytic cyclization, ring-closing metathesis, intramolecular addition, and rearrangement reactions. Representative examples and the featured olfactory investigations will be highlighted, along with some perspectives on future developments in this area.

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Authors+Show Affiliations

Lin Z
School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China.
Huang B
School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China.
Ouyang L
School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China.
Zheng L
School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China.

MeSH

AlkenesAlkynesCatalysisCyclizationCycloaddition ReactionOdorants

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

35684511

Citation

Lin, Zhigeng, et al. "Synthesis of Cyclic Fragrances Via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress." Molecules (Basel, Switzerland), vol. 27, no. 11, 2022.
Lin Z, Huang B, Ouyang L, et al. Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress. Molecules. 2022;27(11).
Lin, Z., Huang, B., Ouyang, L., & Zheng, L. (2022). Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress. Molecules (Basel, Switzerland), 27(11). https://doi.org/10.3390/molecules27113576
Lin Z, et al. Synthesis of Cyclic Fragrances Via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress. Molecules. 2022 Jun 2;27(11) PubMed PMID: 35684511.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress. AU - Lin,Zhigeng, AU - Huang,Baoying, AU - Ouyang,Lufeng, AU - Zheng,Liyao, Y1 - 2022/06/02/ PY - 2022/04/01/received PY - 2022/05/17/revised PY - 2022/05/19/accepted PY - 2022/6/10/entrez PY - 2022/6/11/pubmed PY - 2022/6/14/medline KW - asymmetric organocatalysis KW - carbocycles KW - cascade/tandem/domino reaction KW - cyclization KW - cycloaddition KW - heterocycles KW - natural fragrances KW - synthetic odorants KW - transition-metal catalysis KW - unsaturated hydrocarbons JF - Molecules (Basel, Switzerland) JO - Molecules VL - 27 IS - 11 N2 - With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and heterocycles from readily available unsaturated molecular building blocks, with increased selectivity, atom economy, sustainability and product diversity. In this review, synthetic methods for creating cyclic fragrances, including both natural and synthetic ones, will be discussed, with a focus on the key transformations of alkenes, alkynes, dienes and enynes. Several strategies will be discussed, including cycloaddition, catalytic cyclization, ring-closing metathesis, intramolecular addition, and rearrangement reactions. Representative examples and the featured olfactory investigations will be highlighted, along with some perspectives on future developments in this area. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/35684511/Synthesis_of_Cyclic_Fragrances_via_Transformations_of_Alkenes_Alkynes_and_Enynes:_Strategies_and_Recent_Progress_ DB - PRIME DP - Unbound Medicine ER -