82654-01-1

Upstream product

• 18001-18-8 allyldimethylphenylsilane 
• 186581-53-3 diazomethane 
• 83039-81-0 2-(dimethylphenylsilyl)-3-butenoic acid 

Downstream Products

• 147753-18-2 Methyl (E)-5-Hydroxy-7-phenyl-2-heptenoate 
• 83039-98-9 (E)-5-Phenylsulfanyl-hex-2-enoic acid methyl ester 
• 83039-93-4 (E)-5-Chloro-5-phenyl-pent-2-enoic acid methyl ester 
• 16234-96-1 t-2-Ethyl-1,2,3,4,6,11-hexahydro-c-2,t-4,5,7-tetrahydroxy-6,11-dioxo-r-1-naphthacencarbonsaeure-methylester 
• 19260-55-0 t-2-Ethyl-1,2,3,4,6,11-hexahydro-c-2,5,7-trihydroxy-6,11-dioxo-r-1-naphthacencarbonsaeuremethylester 
• 124438-93-3 nanaomycin A methyl ester 
• 83039-96-7 (E)-4-(1-Chloro-cyclohexyl)-but-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Regioselective Carboxylation of Silicon-Stabilized Allylic Carbanions and the Synthetic Utility of 2-Silyl-3-butenoates

Carbanions of allylic dimethylphenylsilanes show remarkable regioselectivity toward carboxylation with carbon dioxide and methylation with methyl iodide.Methylationn of these compounds occurred preferentially at α position, although allyltrimethylsilane and allyltriphenylsilane are known to give γ selectivity toward the same electrophiles.Moreover, their aluminum "ate" complexes react with carbon dioxide regioselectively at the α position irrespective of methyl substitution pattern of the allylic moieties.The α-carboxylated allylic silanes proved to be useful synthons of 3-(methoxycarbonyl)allyl anions after esterifiaction.

NEW SYNTHETIC APPROACH TO PYRANONAPHTHOQUINONE ANTIBIOTICS, (+/-)-NANAOMYCIN A AND (+/-)-DEOXYFRENOLICIN

The new total synthesis of pyranonaphthoquinone antibiotics, (+/-)-nanaomycin A (1) and (+/-)-deoxyfrenolicin (2), is discussed.The key step in the reaction sequence is Lewis acid mediated Michael addition of acylnaphthoquinone (5) with methyl 2-(dimethylphenylsilyl)-3-butenoate (7).

NEW SYNTHESIS OF METHYL 2-TRIORGANOSILYL-3-BUTENOATES AS A NEW SYNTHON OF 3-METHOXYCARBONYLALLYL ANION

Methyl 2-triorganosilyl-3-butenoates, which are selectively obtained from the carboxylation of the corresponding allylsilanes via allylic aluminates, react with various kinds of electrophiles to give γ substituted (E)-α,β-unsaturated esters in highly regio- and stereoselective manner with the aid of a Lewis acid.