162084-23-3

Upstream product

• 60078-92-4 2,4,4-trimethyl-3-formyl-2-cyclohexen-1-ol 
• 190508-68-0 2,4,4-Trimethyl-3-trityloxymethyl-cyclohex-2-enol 
• 168432-44-8 (+/-)-3-<<(tert-butyldimethylsilyl)oxy>methyl>-2,4,4-trimethylcyclohex-2-en-1-ol 
• 140887-86-1 (+/-)-3-(hydroxymethyl)-2,4,4-trimethylcyclohex-2-en-1-ol 
• 190508-69-1 (+/-)-1,3,3-trimethyl-6-[(prop-2-ynyl)oxy]-2-{[(triphenylmethyl)oxy]methyl}cyclohexene 
• 162084-24-4 (+/-)-2-<<(tert-butyldimethylsilyl)oxy>methyl>-6-<(prop-2-ynyl)oxy>-1,3,3-trimethylcyclohexene 
• 168432-43-7 (+/-)-3-(prop-2-ynyloxy)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde 

Relevant academic research and scientific papers

A synthetic approach to (+/-)-forskolin. Part I. Preparation of key hydrobenzofuran intermediates

In a synthetic approach to (+/-)-forskolin 1, a stereoselective preparation of the unsaturated lactone 2 was envisaged.Propargylic derivatives 18a-c were prepared from available α-ionone 5 and treated with Bu3SnH/AIBN to give the bicyclic vinylstannanes 19a-c in high yield.From these compounds we then performed transmetallation reactions to obtain the 21a-c and 22b homologous derivatives.The two enyne compounds 29 and 30 were then prepared by our previous approach to lactone 2 involving a radical C7-C8 bond formation.In a second radical approach promoted by SmI2, the diol 10, was used to synthesize a potential precursor of the dialdehyde 9. - Keywords: forskolin; tributylstannane; radical cyclization; transmetallation; vinylstannane; vinyl iodide; Pd(0) coupling reaction

Intramolecular coupling reaction promoted by SmI2 in a synthetic approach of forskolin

From available hydroxy-aldehyde 6, propargylic derivative 8 was prepared and treated with Bu3SnH to give in 95% yield the biocyclic vinyl stannone 10. After 10 was converted into the diol 15, this latter was oxidized with the Dess-Martin reagents into the dialdehyde 4. Compound 4 was then submitted to a pinacolic coupling reaction leading to the bicylic cis-diol 3 in a stereospecific manner.