Abstract
The stereoselective total synthesis of garsubellin A is described. The total synthesis was achieved through the stereoselective construction of a bicyclo3.3.1nonane derivative via a three-step sequence: intramolecular cyclopropanation, formation of a germinal dimethyl group, and regioselective ring opening of cyclopropane. To complete the total synthesis of garsubellin A, chemo-And stereoselective hydrogenation to generate the C8 stereogenic center is followed by the formation of the fused tetrahydrofuran ring by a regioselective epoxide-opening reaction with C3 ketone, and finally cross metathesis to construct two prenyl groups.
Original language | English |
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Pages (from-to) | 141-145 |
Number of pages | 5 |
Journal | Journal of Antibiotics |
Volume | 66 |
Issue number | 3 |
DOIs | |
Publication status | Published - 2013 Mar |
Keywords
- cyclopropanation
- garsubellin A
- natural product
- stereoselective synthesis
- total synthesis
ASJC Scopus subject areas
- Pharmacology
- Drug Discovery