Journal
SYNTHESIS-STUTTGART
Volume 50, Issue 15, Pages 2954-2967Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1589541
Keywords
oxatriquinanes; azatriquinanes; vinylogous carbonates; vinylogous carbamates; cascade; tandem radical cyclization; stereoselective synthesis
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Funding
- SERB, New Delhi
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An efficient strategy was developed for the stereoselective construction of oxa- and aza-angular triquinanes employing a cascade 5 - exo - trig radical cyclization to vinylogous carbonates and carbamates. The radical precursors are readily prepared from 2-(hydroxymethyl)cyclopentenone/cyclohexenones. High diastereoselectivity is observed for the formation of angular oxa- and azatriquinanes. Diastereoselectivity drops when six-membered radical precursors are used. The strategy is found to be useful to incorporate synthetically challenging moieties such as spiroindoline, lactone-bearing, and uracil-fused angular triquinanes in a concise manner.
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