Reductive Radical Cyclisations of Bromo Acetals and (Bromomethyl)silyl Ethers of Terpenoid Alcohols

The tin hydride promoted and the reductive vitamin B₁₂ catalysed radical cyclisation of mixed 2-bromo-acetaldehyde acetals and of (2-bromomethyl)dimethylsilyl ethers of allylic terpenoid alcohols has been investigated: 3-oxadeca-5,9-dien-l-yl radicals undergo 5-‘exo’ cyclisation to oxolanes (Scheme 4), 3-oxa-2-siladeca-5,9-dien-1-yl radicals sequential 6-‘endo’→5-‘exo’ tandem cyclisation to cis-3-oxa-4-silabicyclo4.3.0]nonanes (Scheme 5), and 3-oxa-2-silatetradeca-5,9,13-trien-l-yl radicals sequential 6-‘endo’→6-‘endo’→5-‘exo’ triple cyclisation to trans-transoid-trans- 12-oxa-11-silatricyclo7.4.0.0^2,6] tridecanes (Scheme 6).