853246-90-9

Upstream product

• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 5390-04-5 pent-1-yn-5-ol 
• 864909-03-5 dimethyl-{5-methyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-hex-5-en-1-ynyl}-phenyl-silane 
• 198411-11-9 5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne 
• 864909-36-4 3-[(dimethyl-phenyl-silanyl)-ethynyl]-5-methyl-hex-5-en-1-ol 

Relevant academic research and scientific papers

Radical cyclizations leading to the bicyclo[2.2.1]heptane framework: A new radical approach to (±)-(Z)-β-santalol

Tandem radical cyclizations of acyclic iodides, including [3-(2-iodoethyl)-6,10-dimethyl-undeca-5,9-dien-1-ynyl]-dimethylphenylsilane lead in good yields to bicyclo[2.2.1]heptane derivatives. The cascade relies on two sequential radical-mediated 5-exo-cyclizations. The radical approach is illustrated with the total synthesis of racemic-(Z)-β-santalol. The results are remarkable, two fused rings and one stereogenic center are formed in a single operation. A new 'coordinated' hydride appeared to be useful in the cascade.