Total Synthesis of (−)-Himalensine A
The first enantioselective synthesis of (−)-himalensine A has been achieved in 22 steps. The synthesis was enabled by a novel catalytic, enantioselective prototropic shift/furan Diels–Alder (IMDAF) cascade to construct the ACD tricyclic core. A reductive radical cyclization cascade was utilized to build the B ring, and end-game manipulations featuring a molecular oxygen mediated gamma-CH oxidation, a Stetter cyclization to access the pendant cyclopentenone, and a highly chemoselective lactam reduction delivered the natural product target.
Références
- Titre
- Total Synthesis of (−)-Himalensine A
- Type de publication
- Article de revue
- Année de publication
- 2017
- Auteurs
- Shi, Heyao, Michaelides Iacovos N., Darses Benjamin, Jakubec Pavol, Nguyen Quynh Nhu N., Paton Robert S., and Dixon Darren J.
- Revue
- Journal of the American Chemical Society
- Volume
- 139
- Pagination
- 17755–17758
Soumis le 2 octobre 2018