Synthesis of the himandrine skeleton.
The hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination. [reaction: see text]
O'Connor
Patrick D
PD
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
Mander
Lewis N
LN
McLachlan
Matthew M W
MM
D000586:Amination; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D019684:Magnoliopsida / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014197:Trees / Q000737:chemistry*
D006576:Heterocyclic Compounds, 4 or More Rings; C487223:himandrine; D010165:Palladium