403483-52-3

Upstream product

• 13395-73-8 4,4,6-trimethylcyclohex-2-en-1-one 
• 403483-51-2 (2E)-1-iodo-3-(dimethylphenylsilyl)-5-[(tetrahydro-2H-pyran-2-yl)oxy]pentene 
• 51442-80-9 5-(tetrahydro-2H-pyran-2-yloxy)-2-pentyn-1-ol 
• 1073-13-8 4,4-dimethylcyclohexenone 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 74-88-4 methyl iodide 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 500591-01-5 Methanesulfonic acid (E)-3-(dimethyl-phenyl-silanyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester 
• 403483-50-1 (2E)-3-(dimethylphenylsilyl)-5-[(tetrahydro-2H-pyran-2-yl)oxy]penten-1-ol 

Downstream Products

• 403483-54-5 6-{3-(dimethyl-phenyl-silanyl)-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-oxiranylmethyl}-4,4,6-trimethyl-cyclohex-2-enone 
• 403483-57-8 6-(5-hydroxy-3-oxo-pentyl)-4,4,6-trimethyl-cyclohex-2-enone 
• 403483-56-7 4,4,6-trimethyl-6-[3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentyl]-cyclohex-2-enone 

Relevant academic research and scientific papers

Formal synthesis of (+/-)-guanacastepene A.

A 17 step synthesis of 55, a late intermediate in Danishefsky's guanacastepene A synthesis, has been completed in 4% overall yield. Key features include the use of vinylmagnesium bromide in the Pd-catalyzed coupling with triflate 13 to give triene 16 with

A novel extension of the Stork-Jung vinylsilane Robinson annelation procedure for the introduction of the cyclohexene of guanacastepene

A new annelation procedure has been developed in a model system to introduce the cyclohexene ring of guanacastepene. Cyclohexenone 16 is prepared by sequential methylation and alkylation with allylic iodide 15. One-pot epoxidation, protodesilylation and hydrolysis of the THP forms dione 19, which cyclizes with NaOMe to 24 in 57% overall yield. Reduction, Mitsunobu inversion, and selective oxidation of the primary alcohol forms model 29. Phenyldimethylsilyl allylic iodide 36 is easier to make and more stable than trimethylsilyl allylic iodide 6 used by Stork.