185399-84-2

Upstream product

• 185399-83-1 8-((Z)-6-Trimethylsilanyl-hex-3-ene-1,5-diynyl)-1,4-dioxa-spiro[4.5]decan-8-ol 
• 70097-74-4 8-ethynyl-1,4-dioxaspiro[4.5]decan-8-ol 
• 119951-16-5 (Z)-(4-chloro-3-buten-1-ynyl)trimethylsilane 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 185399-85-3 5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5-((Z)-6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 185399-86-4 5-(tert-Butyl-dimethyl-silanyloxy)-2-trifluoromethanesulfonyloxy-5-((Z)-6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 185399-87-5 2-(4-tert-Butoxycarbonylamino-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-5-((Z)-6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-cyclohex-1-enecarboxylic acid methyl ester 
• 185399-88-6 {4-[4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-4-((Z)-6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-cyclohex-1-enyl]-phenyl}-carbamic acid tert-butyl ester 
• 185399-89-7 {4-[4-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-4-((Z)-6-trimethylsilanyl-hex-3-ene-1,5-diynyl)-cyclohex-1-enyl]-phenyl}-carbamic acid tert-butyl ester 
• 185399-90-0 {4-[4-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-4-((Z)-hex-3-ene-1,5-diynyl)-cyclohex-1-enyl]-phenyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of an esperamicin core analog with an epoxide trigger

An esperamicin core analog 4 with an epoxide trigger like that found in the related enediyne, dynemicin, was prepared. Surprisingly, it was found to be relatively stable; the p-aminophenyl substituent did not facilitate epoxide solvolysis to the extent that had been anticipated. A mild acid, pyridinium p-toluenesulfonate, was found to induce solvolysis of 4 and led to the formation of the cycloaromatized product 25.