324769-85-9

Upstream product

• 124-41-4 sodium methylate 
• 506422-90-8 2-bromo-1-hydroxy-p-menth-8-ene 
• 5989-27-5 D-limonene 
• 6485-40-1 (R)-Carvone 
• 185329-56-0 1-methyl-4-(1-methylethenyl)-1,2-cyclohexanediol 

Downstream Products

• 7105-59-1 methyl (3R)-3-isopropenyl-6-oxoheptanoate 
• 1334809-55-0 C₂₉H₃₂Br₂O₄ 

Relevant academic research and scientific papers

Total synthesis of (+)-omphadiol

A smooth transition from (R)-carvone to a β-lactone and then to (+)-omphadiol characterizes the first total synthesis of this sesquiterpene, which was achieved in ten steps and 18 overall yield. All six contiguous stereogenic centers were introduced in a

Direct conversion of tert-β-bromo alcohols to ketones with zinc sulfide and DMSO

tert-β-Bromo alcohols, derived from simple monoterpene hydrocarbons, react with zinc sulfide in dimethyl sulfoxide to afford saturated ketones as the major and hydroxy ketones as the minor products. The reaction involves initial nucleophilic attack by DMSO on the carbon attached to the halogen, which is assisted by electrophilic zinc sulfide. Subsequent Kornblum type oxidation yields the α-hydroxy ketone. On the other hand, abstraction of proton β to the hydroxyl group followed by an attack of the neighboring hydroxyl moiety on the sulfur of the dimethylsulfoxonium intermediate and its subsequent collapse yields an enol, which tautomerizes to a saturated ketone. The latter pathway is predominantly followed.

Conversion of α,β-unsaturated ketones into α-hydroxy ketones using an Mn(III) catalyst, phenylsilane and dioxygen: Acceleration of conjugate hydride reduction by dioxygen

Treatment of a variety of α,β-unsaturated ketones with Mn(dpm)3 (3 mol%)/PhSiH3 (1.3 equiv.)/isopropyl alcohol/O2, followed by reductive work-up with P(OEt)3 resulted in the formation of α-hydroxy-ketones. (C) 2000 Elsevier Science Ltd.

Carbocyclic Construction by the Sigmatropic Rearrangement of Cyclic Sulfonium Ylides. A New Entry for the Stereoselective Synthesis of Substituted Cyclohexanones

The rhodium(II)-catalyzed cyclization of acyclic α-diazo-β-keto esters 1c,d provided stereoselectively the highly substituted cyclohexanones 3c,d respectively, by the sigmatropic rearrangement via stereocontrolled nine-membered allylsulfonium ylides 2c,d.Further elaboration of 3d toward the cyclohexanone 36 accomplished asymmetric formal syntheses of the representative elemanoids, 37 and 38.The compound 3c was transformed into the cyclohexanone 34a and cyclohexene 43, which could serve as the key intermediates for the synthesis of natural products possessing contigously cis-arranged trimethylcyclohexanone and its related moieties, respectively.

Stereoselective Favorskii Rearrangement of Carvone Chlorohydrin; Expedient Synthesis of (+)-Dihydronepetalactone and (+)-Iridomyrmecin

(+)-Dihydronepetalactone and (+)-iridomyrmecin were synthesized from the stereoselective Favorskii rearrangement product of (+)-carvone chlorohydrin.