A new enantioselective approach to total synthesis of the Securinega alkaloids

Application to (-)-norsecurinine and phyllanthine

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

Research output: Contribution to journalArticle

30 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

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Alkaloids
Proline
Derivatives
phyllanthine
norsecurinine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Han, Gyoonhee ; LaPorte, Matthew G. ; Folmer, James J. ; Werner, Kim M. ; Weinreb, Steven M. / A new enantioselective approach to total synthesis of the Securinega alkaloids : Application to (-)-norsecurinine and phyllanthine. In: Angewandte Chemie - International Edition. 2000 ; Vol. 39, No. 1. pp. 237-240.
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A new enantioselective approach to total synthesis of the Securinega alkaloids : Application to (-)-norsecurinine and phyllanthine. / Han, Gyoonhee; LaPorte, Matthew G.; Folmer, James J.; Werner, Kim M.; Weinreb, Steven M.

In: Angewandte Chemie - International Edition, Vol. 39, No. 1, 03.01.2000, p. 237-240.

Research output: Contribution to journalArticle

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