5208-62-8

Upstream product

• 5524-05-0 (-)-dihydrocarvone 
• 78-94-4 methyl vinyl ketone 
• 13567-75-4 (4aR,7R,8aR)-8a-hydroxy-7-isopropenyl-4a-methyloctahydro-2(1H)-naphthalenone 
• 6485-40-1 (R)-Carvone 
• 619-02-3 (-)-dihydrocarvone 
• 192993-38-7 4(R)-isopropenyl-2-methyl-2-(3-oxo-butyl)cyclohexanone 
• 86785-84-4 (4aS,7R)-8a-Hydroxy-7-isopropenyl-4a-methyl-octahydro-naphthalen-2-one 
• 619-02-3 (+)-dihydrocarvone 
• 73890-13-8 11-chloro-14-noreudesm-4-en-3-one 
• 201012-68-2 (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one 
• 6322-49-2 4-chloro-2-butanone 
• 5524-05-0 (2R,5R)-5-isopropenyl-2-methylcyclohexanone 
• 4895-25-4 8aβ-hydroxy-7α-isopropenyl-4aβ-methyl-1,4,4a,5,6,7,8,8a-octahydro-2(3H)-naphthalenone 
• 116499-64-0 (R)-dihydrocarvone 

Downstream Products

• 54878-25-0 (-)-Solavetivone 

Relevant academic research and scientific papers

Agarofuan derivatives, their preparation, pharmaceutical composition containing them and their use as medicine

The compound represented by formula (I), in which the substitutes are defined as in the specification and the claims, or their stereoisomers, the process for preparing them, pharmaceutical composition containing them and their use as medicine.

S-(+)-Carvone as Starting Material in Synthesis (Part 4). Conjugate Addition of Cyanide and Grignard Nucleophiles Followed by Annulation to Functionalized Decalones.

Two conjugate addition/annulation methodologies for S-(+)-carvone are reported.The conjugate addition of Grignard reagents, followed by the Lewis acid catalyzed Michael reaction of the intermediate silyl enol ethers with MVK and cyclization of the diketon

An Improved Synthesis of Homochiral Octalones from (-)-Carvone

A novel diastereoselective route to octalones 3 and 4 has been developed.The key step involves an asymmetric Michael addition of the corresponding chiral imine, derived from R-(+)-dihydrocarvone, to methyl vinyl ketone.

THE CONVERSION OF (-)- AND (+)-DIHYDROCARVONE INTO CHIRAL INTERMEDIATES FOR THE SYNTHESIS OF (-)-POLYGODIAL, (-)-WARBURGANAL AND (-)-MUZIGADIAL

(-)-Dihydrocarvone was converted into (-)-(4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8,trimethylnaphthalene-2(H)-one (1) via an efficient route in which a Wolff-Kishner reduction, accompanied with a double bond isomerisation brought on a major simplification.Ketone 1 is a suitable intermediate for the syntheses of the insectantifeedants (-)-polygodial and (-)-warburganal. (+)-Dihydrocarvone was converted into (+)-(4aR,7S,8aR)-4a,7-dimethyl-8-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2(1H)-one (2), an intermediate ketone for synthesis of (-)-muzigadial.

The Synthesis of Fenical and Sims' Structure of Cycloeudesmol. Stereospecific Total Syntheses of (+)-7β-(1-Hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene, (+)-7α-(1-Hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene, (+)-7β-(1-Hydr...

Stereospecific total syntheses of the four diastereoisomers of Fenical and Sims' structure of cycloeudesmol, (+)-7β-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene (Ia), (+)-7α-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene (Ib), (+)-7β-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aβ-decahydrocyclopropanaphthalene (Ic), and (+/-)-7α-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aβ-decahydrocyclopropanaphthalene (Id), were carried out with the object of establishing the structure of cycloeudesmol.The key step of these syntheses involves the Simmons-Smith reaction directed by the hydroxyl group at the allylic position or the homoallylic position.

An Improved Synthesis of 10β-Methyl-7α-isopropenyl-5β-hydroxy-3-decalone

An improved synthesis of the title compound using tetramethylammonium hydroxide as catalyst is described.

Conformation of Epi-α-cyperone and Related Enones

The conformations of epi-α-cyperone (10-epieudesma-4,11-dien-3-one, 2) and its dihydro and 14-nor analogues (4 and 15, respectively) have been investigated by a combination of lanthanide induced shift reagent 1H NMR, 13C NMR, and high field 1H NMR techniques.Comparison of these spectral data with those of the normal eudesmane derivatives, α-cyperone (1), dihydro-α-cyperone (3), and 14-noreudesm-4-en-3-one (14) clearly shows that the conformations of all six enones are similar with a half-chair conformation for ring A and a chair conformation for ring B.11-Methyl-10-epieudesm-4-en-3-one (5) was prepared either from 5α-hydroxy-10-epieudesm-11-en-3-one (6) or by the Robinson annulation of 2-methyl-5-tert-butylcyclohexanone with ethyl vinyl ketone. 14-Nor-11-methyl-10-epieidesm-4-en-3-one (15) was prepared by the annulation of 2-methyl-5-tert-butylcyclohexanone with methyl vinyl ketone.The 13C lanthanide induced shift and high-field 1H NMR spectra of enones 5 and 13 indicate that these molecules are not conformationally homogeneous.An X-ray structure determination of the oxime of enone 5 showed that in the solid state ring A exists in a envelope conformation and ring B in a twist conformation with a ψ-equatorial tert-butyl group.Crystals of the oxime of 5 belong to the triclinic system, space group P1, with a = 6.290(3) Angstroem, b = 12.010(5) Angstroem, c = 10.341(5) Angstroem, α = 85.20(2) deg, β = 95.56(2) deg, γ = 101.09(2) deg, and Z=2.Atomic positional and thermal parameters were refined by least-squares calculation to R = 0.068 over 1609 observed reflections measured by a diffractometer.