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Angew Chem Int Ed Engl
; 39(1): 237-240, 2000 Jan.
Article
in English
| MEDLINE
| ID: mdl-10649387
ABSTRACT
An inexpensive proline derivative and chiral control feature in the total synthesis of securinega alkaloids (-)-norsecurinine (1) and phyllanthine (2). Key steps in the synthesis of 1 include an intramolecular ketonitrile coupling and application of a radical-based generation of N-acylimines. The total synthesis of 2 utilizes a stereoselective imino Diels - Alder construction of the methoxypiperidine ring.