1,2‐Carbonyl Transposition of a Protected Rubanone: Stereoselective synthesis of bicyclic and tricyclic lactams derived from quinidine | Zendy

Frackenpohl Jens | Zendy; Langer Peter | Zendy; Hoffmann H. Martin R. | Zendy

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1,2‐Carbonyl Transposition of a Protected Rubanone: Stereoselective synthesis of bicyclic and tricyclic lactams derived from quinidine

Author(s) -

Frackenpohl Jens,

Langer Peter,

Hoffmann H. Martin R.

Publication year - 1998

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19980810551

Subject(s) - chemistry , bicyclic molecule , tricyclic , stereoselectivity , lactam , transposition (logic) , stereochemistry , halogenation , organic chemistry , catalysis , linguistics , philosophy

α‐Bromination of 9‐acetoxy rubanone 2 and subsequent reaction with secondary amines gave bicyclic α‐amino ketones as a kinetic product and a 4‐oxa‐1‐azatwistan‐2‐one 6 under thermodynamic conditions. This two‐step procedure represents a concise 1,2‐carbonyl transposition and provides a short route to lactam alkaloids.

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