Abstract
AbstractThe 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‐silabicyclo[4.3.0]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‐silatricyclo[7.4.0.02,6] tridecanes (Scheme 6).
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