Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 9, Pages 3112-3116Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201511659
Keywords
cyclizations; dienynes; natural products; terpenoids; total synthesis
Categories
Funding
- National High Technology Projects 973 [2015CB856200]
- NNSFC [21561142002, 21472010, 21232001]
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Reported is the first scalable synthesis of rac-jungermannenonesB and C starting from the commercially available and inexpensive geraniol in 10 and 9 steps, respectively. The unique jungermannenone framework is rapidly assembled by an unprecedented regioselective 1,6-dienyne reductive cyclization reaction which proceeds through a vinyl radical cyclization/allylic radical isomerization mechanism. DFT calculations explain the high regioselectivity observed in the 1,6-dienyne reductive radical cyclization.
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