Synthesis of (-)-ambrox from ℓ-abietic acid

Koyama, Hiroo; Kaku, Yumiko; Ohno, Masaji

doi:10.1016/s0040-4039(00)96229-4

Cited by 44 publications

(27 citation statements)

References 26 publications

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“…The crude product was dissolved in EtOAc (20.0 mL) and was washed with water. The organic layer was dried over anhydrous MgSO 4 m, 1H, H1), 1.22 (s, 3H, H-19 …”

Section: Synthesis Of 14 From 13mentioning

confidence: 99%

“…The reaction mixture was filtered and the organic phase washed with a saturated NaHCO 3 solution. The organic layer was dried over anhydrous MgSO 4 ).…”

Section: Synthesis Of 20 From 17mentioning

confidence: 99%

“…2 This acid has been used widely as an enantiomerically pure starting material in organic synthesis. 3 Examples are the syntheses of Ambrox ® , warburganal 4 and some other sesquiterpenes. 5 In order to evaluate the biological activities of the compounds obtained by modifying the framework of methyl ester 1b, we first synthesized the stable ozonide 2 that showed activity against some lines of non-small lung cell, melanoma and breast cancers.…”

Section: Introductionmentioning

confidence: 99%

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Chemical transformation of abietic acid to new chiral derivatives

Santos

Zukerman-Schpector

Imamura

2003

J. Braz. Chem. Soc.

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Neste trabalho descrevemos as reações de transformações químicas do anel C do ácido abiético (1a) com o objetivo de gerar novos síntons quirais. A partir do intermediário ceto-aldeído 9, obtido através da reação de ozonólise do abietato de metila (1b), foram sintetizados derivados bicíclicos tais como 14, 15 e 16 e um novo diterpeno tetracíclico 4. Foram também sintetizados, a partir 17, novos derivados contendo esqueleto abeo-abietano [6,6,5] tais como 19 e 20.Chemical transformations of the C-ring abietic acid (1a) for the preparation of some new chiral synthons are described. From the intermediate keto-aldehyde 9, readily available from 1b through the ozonide 2, the new tetracyclic diterpene 4 was synthesized. Additionally, from 13 and 17, previously prepared from 2, the bicyclic compounds 14, 15 and 16 and the derivatives containing the abeo-abietane [6,6,5] framework 19 and 20 were also synthesized.

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“…The crude product was dissolved in EtOAc (20.0 mL) and was washed with water. The organic layer was dried over anhydrous MgSO 4 m, 1H, H1), 1.22 (s, 3H, H-19 …”

Section: Synthesis Of 14 From 13mentioning

confidence: 99%

“…The reaction mixture was filtered and the organic phase washed with a saturated NaHCO 3 solution. The organic layer was dried over anhydrous MgSO 4 ).…”

Section: Synthesis Of 20 From 17mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chemical transformation of abietic acid to new chiral derivatives

Santos

Zukerman-Schpector

Imamura

2003

J. Braz. Chem. Soc.

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“…However, its limited availability has stimulated several studies aimed at employing other natural raw materials for synthesis of compounds with this fragrance. 2 Longifolene is one of the most abundant sesquiterpene hydrocarbons produced by coniferous trees of the family Pinaceae. It may therefore represent a good starting material for the synthesis of compounds with amber-like odour.…”

Section: Introductionmentioning

confidence: 99%

“…75% of longifolene, GC), isolated by fractional distillation of the residue of Polish turpentine oil, 6 was transformed to 6-acetyl-2,8-dimethyl-tricyclo[4.4.0.0 2,8 ]decane in the following reaction Scheme 1:…”

mentioning

confidence: 99%

12-nor-alloisolongifolan-11-one, a ketone with amber-like odour from longifolene

Kula

Masarweh

1998

Flavour Fragr. J.

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Formation of Alkanes and Arenes by Reduction

Larock

Zhang

2017

Comprehensive Organic Transformations

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Cyclic Alkanes Arenes Alkenes Alkynes Organic Halides Amines and Derivatives Nitro Compounds Ethers Alcohols and Phenols Sulfur Compounds Selenium and Tellurium Compounds Aldehydes and Ketones Acetals Carboxylic Acids Acid Halides Anhydrides Esters and Lactones Nitriles Isonitriles

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Synthesis of (-)-ambrox from ℓ-abietic acid

Cited by 44 publications

References 26 publications

Chemical transformation of abietic acid to new chiral derivatives

Chemical transformation of abietic acid to new chiral derivatives

12-nor-alloisolongifolan-11-one, a ketone with amber-like odour from longifolene

Formation of Alkanes and Arenes by Reduction

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