204275-52-5

Upstream product

• 35998-30-2 3-(phenylsulfanyl)-3,4-dihydrofuran-2-one 
• 179112-70-0 2-((5E,9E)-12-Iodo-5,9-dimethyl-dodeca-5,9-dienyloxy)-tetrahydro-pyran 
• 179112-69-7 2-((5E,9E)-12-Bromo-5,9-dimethyl-dodeca-5,9-dienyloxy)-tetrahydro-pyran 
• 204275-51-4 (E)-2-Cyclopropyl-6-methyl-10-(tetrahydro-pyran-2-yloxy)-dec-5-en-2-ol 
• 179112-72-2 2-((E)-8-Bromo-5-methyl-oct-5-enyloxy)-tetrahydro-pyran 
• 179112-62-0 (5E,9E)-12-Bromo-5,9-dimethyl-dodeca-5,9-dien-1-ol 
• 127895-40-3 (E)-8-bromo-5-methyloct-5-en-1-ol 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 179112-71-1 (5E,9E)-5,9-Dimethyl-12-(2-oxo-2,5-dihydro-furan-3-yl)-dodeca-5,9-dieneselenoic acid Se-phenyl ester 

Relevant academic research and scientific papers

Cascade radical processes leading to polycycle constructions. The total synthesis of spongian-16-one

A concise total synthesis of the marine sponge metabolite spongian-16-one 1, which features a novel cascade of three consecutive 6-endo-trig radical cyclisations from a polyene acyl radical intermediate as a key step, viz 9 → 10, is described.

Cascade radical cyclisations leading to polycyclic diterpenes. Total synthesis of (±)-spongian-16-one

A cascade of three consecutive 6-endo-trig radical cyclisations from the polyene acyl radical intermediate 12 derived from the selenoate 11 is used to construct the trans,anti,trans,anti,cis-tetracyclic keto lactone 20 in one step. Manipulation of the ketone function in 20 to the corresponding gem-dimethyl substituted carbon then completed a concise synthesis of the marine metabolite spongian-16-one 1.