179601-53-7

Upstream product

• 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 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 179331-61-4 (1S,2S,3R)-2-(3-Hydroxy-2-hydroxymethyl-propenyl)-3-isopropyl-6-oxo-cyclohexanecarboxylic acid methyl ester 

Downstream Products

• 191987-07-2 (5R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-2-(diethoxy-phosphoryloxy)-5-isopropyl-cyclohex-1-enecarboxylic acid methyl ester 
• 191987-08-3 (5R,6S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-5-isopropyl-2-trimethylsilanylmethyl-cyclohex-1-enecarboxylic acid methyl ester 
• 191987-09-4 (5R,6S)-6-(3-Acetoxy-2-acetoxymethyl-propenyl)-5-isopropyl-2-trimethylsilanylmethyl-cyclohex-1-enecarboxylic acid methyl ester 
• 191987-10-7 (1S,2S,3R)-2-(3-Acetoxy-2-acetoxymethyl-propenyl)-3-isopropyl-6-methylene-cyclohexanecarboxylic acid methyl ester 
• 57710-57-3 1,5a,6,7,8,9a-hexahydro-6-(1-methyl-ethyl)-1-oxo-spiro<2-benzoxepin-9(3H),2'oxirane>-4-carboxylic acid (heptelidic acid) 

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.