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Novel Synthesis of Trisubstituted Olefins for the Preparation of the C16–C30 Fragment of Dolabelide C
- Tiniakos, Alexander F., Wittmann, Stéphane, Audic, Alexandre, Prunet, Joëlle
- Organic letters 2018 v.21 no.3 pp. 589-592
- alcohols, alkenes, chemical reactions, chemical structure
- A silicon-tether ring-closing metathesis strategy is reported for the synthesis of trisubstituted olefins flanked by allylic or homoallylic alcohols, which are difficult to obtain by classical ring-closing or cross-metathesis reactions. In addition, a novel Peterson olefination reaction has been developed for the preparation of the allyldimethylsilane precursors, which are versatile synthetic intermediates. This method was then applied to the synthesis of the C16–C30 fragment of dolabelide C.