Synthesis of ambergris fragrance chemicals from sclareol, involving palladium catalysed key steps

Coste-Manière, Ivan; Zahra, Jean-Pierre; Waegell, B.

doi:10.1016/0040-4039(88)85323-1

Cited by 56 publications

(13 citation statements)

References 21 publications

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“…26 The transformation of diol 13 into ether 14 (ambrox) is the last step in many synthetic sequences for preparing this valuable odorant substance. 27 The direct conversion of sclareol (24), an allylic alcohol prone to elimination reactions, into manoyl oxide (25a), utilizing phosphoric acid as a cyclizing reagent, has been reported by CosteManiere et al; 34 when we repeated the described procedure a complex mixture of compounds was always obtained. All the attempts to cyclize 24 to 25a by acid treatment, even under mild conditions, gave unsatisfactory results; the treatment of 24 with CAN led smoothly to a mixture of manoyl (25a) and 13-epimanoyl oxide (25b) in a 2.5-3.0:1 relation, depending upon the temperature.…”

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confidence: 90%

Cerium(IV) Ammonium Nitrate (CAN): A Very Efficient Reagent for the Synthesis of Tertiary Ethers

Álvarez-Manzaneda¹,

Chaboun²,

Alvarez³

et al. 2006

Synlett

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R e a g e n t f o r t h e S y n t h e s i s o f T e r t i a r y E t h e r sAbstract: Treatment of tertiary 1,4-and 1,5-diols with cerium ammonium nitrate at room temperature led to the corresponding tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Utilizing this methodology, manoyl oxide (25a) and a variety of fragrant compounds, such as linalool oxide (8), caparrapi oxide (12), ambrox (14) and other related amber-gris-type odorants have been synthesized; 16 examples are described.

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confidence: 90%

Cerium(IV) Ammonium Nitrate (CAN): A Very Efficient Reagent for the Synthesis of Tertiary Ethers

Álvarez-Manzaneda¹,

Chaboun²,

Alvarez³

et al. 2006

Synlett

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“…The palladium-catalyzed 1,4-elimination of allylic alcohol derivatives to the corresponding 1,3-dienes is a well-known synthetic transformation [8] which has been applied in the synthesis of fragrance precursors such as Myrcene [9] and Abienol [10].…”

Section: Selective Synthesis Of Homomyrcenementioning

confidence: 99%

Recent Optimization Highlights of the Georgywood Process

Barras¹,

Bourdin²,

Schröder³

2006

Chimia

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Alternative procedures to the industrial process by which Georgywood ® is presently prepared on a multiton scale have been investigated. these give the crucial homomyrcene precursor 5a and target compound 1 with greatly improved selectivities. homomyrcene 5a was prepared with much better yield and selectivity by converting methylgeraniol 4 into an allylic carbonate, followed by a solvent-free palladium-catalyzed 1,4-elimination. in the final 1,5-diene cyclization, excellent selectivities were achieved by replacing Brønsted acid h 3 Po 4 by meAlcl 2 . this requires preparation, safety measures and an in-situ conversion of stoichiometric amounts of the pyrophoric Lewis acid. recently, an in situ preparation of meAlcl 2 from Alme 3 and its catalytic use became possible.

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“…Thus, reduction of compound 32 with NaBH 4 in i-PrOH for 2 h led to product 39, which can be used to semisynthesize warburganal [34] [35] and (À)-Ambrox [36] [37]. Therefore, compound 39 was treated with TsCl in pyridine to convert the OH group into a good leaving group, but under these reaction conditions, only the conjugated diene 40 [14] was obtained through elimination.…”

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confidence: 99%

Bioactive Compounds with Added Value Prepared from Terpenes Contained in Solid Wastes from the Olive Oil Industry

Parra¹,

López²,

Garcı́a-Granados³

2010

Chemistry & Biodiversity

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Starting from solid wastes from two-phase olive-oil extraction, the pentacyclic triterpenes oleanolic acid and maslinic acid were isolated. These natural compounds were transformed into methyl olean-12-en-28-oate (5), which then was transformed into several seco-C-ring triterpene compounds by chemical and photolytic modifications. The triene seco-products were fragmented through several oxidative procedures to produce, simultaneously, cis- and trans-decalin derivatives, both potential synthons for bioactive compounds. The chemical behavior of the isolated fragments was investigated, and a suitable approach to several low-molecular-weight terpenes was performed. These are interesting processes for the value-addition to solid waste from the olive-oil industry.

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Synthesis of ambergris fragrance chemicals from sclareol, involving palladium catalysed key steps

Cited by 56 publications

References 21 publications

Cerium(IV) Ammonium Nitrate (CAN): A Very Efficient Reagent for the Synthesis of Tertiary Ethers

Cerium(IV) Ammonium Nitrate (CAN): A Very Efficient Reagent for the Synthesis of Tertiary Ethers

Recent Optimization Highlights of the Georgywood Process

Bioactive Compounds with Added Value Prepared from Terpenes Contained in Solid Wastes from the Olive Oil Industry

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