179331-61-4

Upstream product

• 67-56-1 methanol 
• 179331-58-9 (1S,2S,3R)-2-(2,2-Dimethyl-[1,3]dioxan-5-ylidenemethyl)-3-isopropyl-6-oxo-cyclohexanecarboxylic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 

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 

Relevant academic research and scientific papers

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

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.