Abstract
The asymmetric total synthesis of farnesin, a rearranged ent-kaurenoid, was achieved through a convergent approach involving photo-Nazarov and intramolecular aldol cyclizations to build the syn-syn-syn hydrofluorenol ABC ring system and bicyclo[3.2.1]octane CD ring system in the first application of a UV-light-induced excited-state Nazarov cyclization of a non-aromatic dicyclic divinyl ketone in a total synthesis. Unlike the conventional acid-promoted ground-state Nazarov reaction, the excited-state Nazarov reaction enables stereospecific formation of the highly strained syn-syn-syn-fused hydrofluorenone scaffold through a disrotatory cyclization.
| Original language | English |
|---|---|
| Pages (from-to) | 7444-7449 |
| Number of pages | 6 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 59 |
| Issue number | 19 |
| DOIs | |
| State | Published - 4 May 2020 |
Keywords
- Nazarov cyclization
- polycycles
- strained molecules
- terpenoids
- total synthesis