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
Revue
Journal of the American Chemical Society
Volume
139
Pagination
17755–17758
Soumis le 2 octobre 2018