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

doi:10.1002/(SICI)1521-3773(20000103)39

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

Chemistry

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

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 language	English (US)
Pages (from-to)	237-240
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	1
DOIs	https://doi.org/10.1002/(SICI)1521-3773(20000103)39
State	Published - Jan 3 2000

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1002/(SICI)1521-3773(20000103)39

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AU - Weinreb, Steven M.

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

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