Helvetica Chimica Acta p. 146 - 162 (1991)
Update date:2022-07-29
Topics:
Lee, Edward R.
Lakomy, Ivo
Bigler, Peter
Scheffold, Rolf
The tin hydride promoted and the reductive vitamin B12 catalysed radical cyclisation of mixed 2-bromoacetaldehyde acetals and of (2-bromomethyl)dimethylsilyl ethers of allylic terpenoid alcohols has been investigated: 3-oxadeca-5,9-dien-1-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-1-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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