123809-45-0

Upstream product

• 81306-20-9 (5aR,9aR)-1,3-Dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 
• 126087-79-4 3-phenylthio-6,6,9aβ-trimethyl-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2->furan 
• 89708-57-6 (4aS,8aS)-2-[1-Butylsulfanyl-meth-(E)-ylidene]-5,5,8a-trimethyl-octahydro-naphthalen-1-one 
• 50490-43-2 (+/-)-euryfuran 
• 77630-13-8 (4aS,8aS)-5,5,8a-Trimethyl-1-oxo-decahydro-naphthalene-2-carbaldehyde 
• 81306-30-1 (5aR,9aR)-3-Butylsulfanyl-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan 
• 126113-04-0 1-cyano-2-(phenylthiomethylene)-5,5,8αβ-trimethyl-1-trimethylsilyloxy-trans-perhydronaphthalen 
• 126087-78-3 2-phenylthiomethyl-5,5,8αβ-trimethyl-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxaldehyde 
• 114701-17-6 trans-2-<(phenylthio)methylene>-5,5,8a-trimethylperhydro-1(2H)-naphthalenone 
• 89656-04-2 (4aR,8aR)-1-Benzenesulfinylmethyl-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde 
• 16776-05-9 (+-)-5,5,8a-trimethyl-(4ar,8at)-octahydro-naphthalen-1-one 

Relevant academic research and scientific papers

A new approach to annelated butenolides. The total synthesis of (+/-)-isodrimenin

A new approach to annelated butenolides has been developed starting from trans-5,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1(2H)-naphthalenone (3) and cyclohexanones.A reaction sequence consisting of formylation of the enolates of these ketones, protection of the formyl group as its dioxolane and addition of methoxy(phenylthio)methyllithium has been used to introduce the necessary functionalized carbon atoms.Rearrangement of the adduct to α-(phenylthio)aldehydes, followed by hydrolysis of the dioxolane, resulted in the formation of butenolides.The method has been demonstrated in the total synthesis of (+/-)-isodrimenin.Direct hydrolysis of the adducts, obtained after addition of methoxy(phenylthio)methyllithium, followed by treatment with acid, also gave butenolides.

A Regioselective Annulation of Butenolides. The Total Synthesis of (+/-) Confertifolin

γ-(Phenylsulfinyl)-α,β-unsaturated aldehydes 2, prepared from α-(n-butylthio)methylene ketones 1 via addition of lithium followed by hydrolysis and oxidation, are converted into butenolides 4 or 5 depending upon the reaction conditions.

DIISOBUTYLALUMINUM HYDRIDE REDUCTION OF UNSATURATED SYLYLCYANOHYDRINS: A NEW ENTRY TO CONFERTIFOLIN

A new entry to the drimane-related sesquiterpene Confertifolin is reported.The key step involves the conversion of a β-phenylthio-α,β-unsaturated ketone into the corresponding silylcyanohydrin followed by diisobutylaluminum hydride reduction to the homologous α,β-unsaturated aldehyde.

SYNTHESIS OF EURYFURAN, VALDIVIOLIDE, AND CONFERTIFOLIN

Starting from 5,5,9-trimethyl-trans-1-decalone (4), short and highly efficient synthesis of three drimane natural products, euryfuran (1), valdiviolide (2), and confertifolin (3) have been developed.