213924-91-5

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 213924-80-2 5-Hydroxy-2-methyl-5-((Z)-6-triisopropylsilanyl-hex-3-ene-1,5-diynyl)-cyclohex-1-enecarboxylic acid ethyl ester 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 14160-65-7 ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate 
• 76379-88-9 8-Methyl-1,4-dioxa-spiro[4.5]dec-7-ene-7-carboxylic acid ethyl ester 
• 98046-49-2 2-Methyl-5-oxo-cyclohex-1-enecarboxylic acid ethyl ester 
• 213924-79-9 ethyl 8-(((trifluoromethyl)sulfonyl)oxy)-1,4-dioxaspiro[4.5]dec-7-ene-7-carboxylate 

Downstream Products

• 213924-81-3 [5-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-((Z)-6-triisopropylsilanyl-hex-3-ene-1,5-diynyl)-cyclohex-1-enyl]-methanol 
• 213924-82-4 5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde 
• 213924-92-6 [5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enyl]-methanol 
• 213924-83-5 5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde 
• 213924-93-7 [5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enyl]-methanol 
• 213924-94-8 (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1⁽¹²⁾,5-diene-3,7-diyn-11-yl ester 

Relevant academic research and scientific papers

Taxamycin studies: Synthesis of taxoid-calicheamicin hybrids

The synthesis of the bicyclic enediyne compounds 14-18 is described. The bicyclo[7.3.1]trideca-4,9-dien-2,6-diynes (21) are calicheamicin-taxoid mimics, that possess the Taxotere side chain and an enediyne core. Cyclization of the iodo-aldehyde 13 [CrCl2(THF)2] afforded the bicyclic alcohol 14 as a single diastereomer (76%) and allylic oxidation (SeO2) followed by reaction with the oxazolidine intermediate 19, resolution and hydrolysis provided the taxamycins 21.