Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 6, Pages 1754-1758Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201410806
Keywords
bridged ring systems; cycloaddition; diastereoselectivity; endo selectivity; natural products
Categories
Funding
- Natural Science Foundation of China [21172009, 21402083, 21472081]
- Natural Science Foundation of Guangdong [S2012010010611]
- Shenzhen Basic Research Program [JCYJ20130329180259934]
Ask authors/readers for more resources
A typeII intramolecular oxidopyrylium-mediated [5+2] cycloaddition reaction allows the efficient and diastereoselective formation of various highly functionalized and synthetically challenging bridged seven-membered ring systems (such as bicyclo[4.4.1]undecane, bicyclo[4.3.1]decane, bicyclo[5.4.1]dodecane, and bicyclo[6.4.1]]tridecane). This simple, thermal, direct transformation has a broad substrate scope and is high yielding, with high functional-group tolerance and unique endo selectivity. The highly strained tricyclic cores of ingenol mebutate (picato) and cyclocitrinol are synthesized efficiently and diastereoselectively using this methodology.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available