179331-58-9

Upstream product

• 170808-41-0 (1R,2R,3S,4S)-<3--2-bornyl>-(5R)-2-oxo-5-isopropylcyclohexenecarboxylate 
• 179331-57-8 5-(bromomethylene)-2,2-dimethyl-1,3-dioxane 
• 217486-74-3 5-Bromo-5-bromomethyl-2,2-dimethyl-[1,3]dioxane 
• 3190-50-9 2,5-dimethyl-5-methylene-1,3-dioxane 

Downstream Products

• 179601-53-7 (1S,2S,3R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-3-isopropyl-6-oxo-cyclohexanecarboxylic acid methyl ester 
• 179331-61-4 (1S,2S,3R)-2-(3-Hydroxy-2-hydroxymethyl-propenyl)-3-isopropyl-6-oxo-cyclohexanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

A key step towards EPC synthesis of (+)-heptelidic acid

Absolute configuration of enoates 3n and 4n, which have been prepared as chiral building blocks for the EPC synthesis of the antibiotic (+)-heptelidic acid, was determined by X-ray structure analysis. Conjugate addition of an acetal protected vinylcuprate to the 5'R configurated enoate 3n gave adduct 9n as a single diastereomer in 79% yield. Further, cleavage of the auxiliary and of the acetal protecting group from 9n were studied. Finally, we obtained the silyl protected α-ketoester 13 in enantiomerically pure form, which is a known intermediate for the synthesis of heptelidic acid.

EPC Synthesis of (+)-Heptelidic Acid

An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which g