75697-98-2

Upstream product

• 104543-27-3 2-isopropenyl-5-methyl-4-hexenal ethylene glycol acetal 
• 119045-78-2 2-isopropenyl-5-methyl-4-hexenal dimethylhydrazone 
• 121726-27-0 methyl-3 N-phenyl butene-3 imidothioate de methyle 
• 91930-21-1 isopropenyl-2 methyl-5 hexene-4 dithioate de methyle 
• 91914-69-1 3-(Ethylsulfanyl-methylsulfanyl-methyl)-2,6-dimethyl-hepta-1,5-diene 
• 115-18-4 2-methyl-3-buten-2-ol 
• 31525-65-2 3-methyl-but-2-enal dimethyl acetal 
• 58461-27-1 (+/-)-lavandulol 
• 25905-14-0 lavandulyl acetate 
• 41004-19-7 1-iodo-3-methyl-but-2-ene 
• 870-63-3 prenyl bromide 
• 91914-51-1 isopropenyl-2 methyl-5 hexene-4 thioimidate de methyle 
• 91914-47-5 N-(methyl-3 methylthio-l butadiene-1,3 yl) N-trimethylsilyl aniline 

Downstream Products

• 58461-27-1 (+/-)-lavandulol 
• 73335-87-2 [(2E,4E)-9-Hydroxy-6-(1-hydroxy-1-methyl-ethyl)-3,9-dimethyl-deca-2,4-dienyl]-triphenyl-phosphonium; bromide 
• 32719-43-0 (2S,3E,2'S,3'E)-2,2'-bis-(3-hydroxy-3-methyl-butyl)-3,4,3',4'-tetradehydro-2H,2'H-ψ,ψ-carotene-1,1'-diol 

Relevant academic research and scientific papers

A Practical Domino-Claisen–Cope Sequence in the Synthesis of New Blooming Citrus and Potent Floral Rose Alcohols

Fifty years after its first discovery by Alan Francis Thomas, we describe a versatile, metal and pressure-free domino-Claisen–Cope rearrangement using the readily available α,β-unsaturated aldehydes 5 or their acetals 5′ and allylic alcohols 6. This transformation provides a convenient access to a large number of radiant citrus and floral rosy odorants. Odor profiles of novel floral rosy and citrus alcohols 13, 14, and 16 were studied. Compound 14ba has a floral, rosy, geranium-like character and shows unique performance and diffusiveness. Compound 16ba has a clear main citrus odor character with a clean green grapefruit/rhubarb connotation. Both odorants have been successfully introduced to perfumery recently as Rosyfolia (14ba) and Pomelol (16ba).

Fungal mediated kinetic resolution of racemic acetates to (R)-alcohols using Fusarium proliferatum

Fungal mediated kinetic resolution of seven acyclic/aromatic acetates was achieved using Fusarium proliferatum to furnish (R)-alcohols in high enantiomeric excess (>95%). The kinetic resolution was established as one-pot two-step de-esterification/oxidation biocatalytic process. Further, the preparative scale synthesis of (R)-(+)-1-phenylethanol was accomplished through de-esterification/oxidation of (±)-1-phenylethyl acetate using the whole cell of F. proliferatum NCIM 1105.

Carbon-carbon bond formation employing organoiron reagents. Syntheses of lavandulol and red scale pheromone

Some aspects of the chemistry of (η1-allyl)Fp complexes [Fp =η5-C5H5Fe(CO)2] are briefly reviewed, especially the means available for their elaboration. The range of electrophiles which react with (η1-allyl)Fp complexes has been enlarged to include allyl iodides. Two examples of this reaction are given, the first leading to lavandulol 9, the second providing a short synthesis of the red scale pheromone (R,S-15).

METALLATION ET ALKYLATION DES THIOIMIDOESTERS: APPLICATION EN SYNTHESE

Alkylation of delocalized anions resulting from metallation of N-phenyl thioimidoesters (precursors of dithioesters and thiolesters) takes place on nitrogen with "saturated" thioimidoesters (alkane thiomidates).On the contrary, unsaturated thiomidoesters (α or β-ethylenic, α-arylated) are regioselectively alkylated on the α carbon atom by alkyl or allylic halides.The possibilities for synthesis offered by successive uses of the reactivities of thioimidoester and dithioester functions (allowing in particular two electrophilic additions on two vicinal carbons) are illustrated by syntheses of terpenic compounds lavandual (and lavandulol) and ar-curcumene.