174060-96-9

Upstream product

• 26976-89-6 5-(4-methoxyphenyl)furan-2(5H)-one 
• 917-54-4 methyllithium 
• 100-07-2 4-methoxy-benzoyl chloride 
• 259655-88-4 N,N-diisopropyl-4-(4-methoxyphenyl)-3-methyl-4-oxobutanamide 

Downstream Products

• 173913-49-0 (2R,3R,4S)-2-bromo-4-(p-methoxyphenyl)-3-methyl-4-butanolide 
• 157719-55-6 (2S,3S,4S)-2-azido-4-(p-methoxyphenyl)-3-methyl-4-butanolide 

Relevant academic research and scientific papers

Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin

An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse γ-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (-)-nicotlactone B and (-)-galbacin, have thus been obtained.

Highly diastereoselective reduction of γ-keto amides: Diastereoselective synthesis of γ-butyrolactones with contiguous chiral centers

Diastereoselective reduction of γ-keto amides, which were easily prepared by the reaction of a zinc homoenolate of butanamide with acid chlorides in the presence of Pd(0) catalyst, was achieved. Cyclization of the products, γ-hydroxy amides, under various