New Preparation Methods for α‐Damascone, γ‐Damascone, and β‐Damascenone using Pyronenes

Boulin, Bertrand; Taran, M.; Miguel, B. Arreguy-San; Delmond, B.

doi:10.1080/00397910701462898

Cited by 8 publications

(9 citation statements)

References 50 publications

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“…As a final point, it is worth noting that a new synthetic entry to racemic α-damascone, γ-damascone and β-damascenone has been described [56]. Accordingly, γ-pyronene 60 and δ-pyronene 61 , were regioselectively epoxidized to give epoxides 62 and 63 , respectively (Figure 11).…”

Section: New Synthetic Approaches To the Most Relevant Classes Of mentioning

confidence: 98%

Recent Advances in the Synthesis of Carotenoid-Derived Flavours and Fragrances

Serra

2015

Molecules

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Carotenoids are important isoprenoid compounds whose oxidative degradation produces a plethora of smaller derivatives, called apocarotenoids, which possess a range of different chemical structures and biological activities. Among these natural products, compounds having less than 15 carbon atoms in their frameworks are often relevant flavours or fragrances and their manufacturing represents an important economic resource for chemical companies. The strict correlation between stereochemical structure and odour has made the stereospecific synthesis of the latter biological active compounds increasingly important. In this review, the recent advances on the synthesis of the most relevant carotenoid-derived flavours and fragrances are discussed. In particular, the new synthetic methods that have given new and innovative perspectives from a scientific standpoint and the preparative approaches that might possess industrial importance are described thoroughly.

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Section: New Synthetic Approaches To the Most Relevant Classes Of mentioning

confidence: 98%

Recent Advances in the Synthesis of Carotenoid-Derived Flavours and Fragrances

Serra

2015

Molecules

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“…[186] Other cyclic compounds of particular interest are dand gpyronenes. [187,188] They are used as important starting material in the synthesis of damascones, commonly named rose ketones, and are among the most of sought-after fragrant compounds in the perfume industry for their pleasant flower fragrance with fruity tones. [189] For instance, d-pyronene is industrially available by acid-induced cyclization of myrcene sulfone (Scheme 18).…”

Section: Cyclic Products Via Rearrangementmentioning

confidence: 99%

Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review

2009

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Currently, a shift towards chemical products derived from renewable, biological feedstocks is observed more and more. However, substantial differences with traditional feedstocks, such as their "hyperfunctionalization," ethical problems caused by competition with foods, and problems with a constant qualitative/quantitative availability of the natural products, occasionally complicate the large-scale market entry of renewable resources. In this context the vast family of terpenes is often not taken into consideration, although the terpenes have been known for hundreds of years as components of essential oils obtained from leaves, flowers, and fruits of many plants. The simple acyclic monoterpenes, particularly the industrially available myrcene, provide a classical chemistry similar to unsaturated hydrocarbons already known from oil and gas. Hence, this Review is aimed at reviving myrcene as a renewable compound suitable for sustainable chemistry in the area of fine chemicals. The versatility of the unsaturated C(10)-hydrocarbon myrcene, leading to products with several different areas of application, is pointed out.

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“…Later, it was recognized as an important constituent not only in perfumes but also in food products and beverages . Although its structure is relatively simple among the most heavily researched aroma compounds, the synthesis is not as easy as expected [4‐12] . Several more or less complicated approaches have been explored to construct its C 13 megastigmane skeleton ( A , Figure.…”

Section: Introductionmentioning

confidence: 99%

“…Several more or less complicated approaches have been explored to construct its C 13 megastigmane skeleton ( A , Figure. ), such as homologation reactions of (C 10 + C 3 ), (C 9 + C 4 ) and (C 11 + C 2 ) . Up to now, the accesses start from the inexpensive, naturally abundant C 10 species (e.g.…”

Section: Introductionmentioning

confidence: 99%

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Solvent effect on the debromination/dehydrobromination of bromo‐damascone

Cheng

Ren

et al. 2016

Flavour & Fragrance J

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The dehydrogenative synthesis of β‐damascenone from β‐damascone via the related allyl bromide intermediate was studied in depth. The requisite dehydrobromination thereof was found strongly solvent system dependent. Under respective conditions, the product was identified as dehydrogenation‐derived a, 4‐alkoxy‐derived b and 4‐oxo‐derived c, accordingly. In addition, the conversion from b to a was successfully accomplished, thereby offering an alternative access (with one step more) to reach β‐damascenone. Copyright © 2016 John Wiley & Sons, Ltd.

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New Preparation Methods for α‐Damascone, γ‐Damascone, and β‐Damascenone using Pyronenes

Cited by 8 publications

References 50 publications

Recent Advances in the Synthesis of Carotenoid-Derived Flavours and Fragrances

Recent Advances in the Synthesis of Carotenoid-Derived Flavours and Fragrances

Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review

Solvent effect on the debromination/dehydrobromination of bromo‐damascone

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