A new enantioselective approach to total synthesis of the Securinega alkaloids: Application to (-)-norsecurinine and phyllanthine

Han Gyoonhee, Matthew G. LaPorte, James J. Folmer, Kim M. Werner, Steven M. Weinreb

Research output: Contribution to journalArticle

31 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)237-240
Number of pages4
JournalAngewandte Chemie - International Edition
Volume39
Issue number1
DOIs
Publication statusPublished - 2000 Jan 3

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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