Synthesis of the Himandrine Skeleton | Zendy

P. D. T. O’Connor | Zendy; Lewis N. Mander | Zendy; Matthew M. W. McLachlan | Zendy

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Synthesis of the Himandrine Skeleton

Author(s) -

P. D. T. O’Connor,

Lewis N. Mander,

Matthew M. W. McLachlan

Publication year - 2004

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol036308n

Subject(s) - chemistry , curtius rearrangement , amination , intramolecular force , nucleophile , cycloaddition , alkene , reductive amination , skeleton (computer programming) , birch reduction , diels–alder reaction , stereochemistry , organic chemistry , catalysis , computer science , programming language

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]

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