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A New Enantioselective Approach to Total Synthesis of the Securinega Alkaloids: Application to (−)‐Norsecurinine and Phyllanthine
Author(s) -
Han Gyoonhee,
LaPorte Matthew G.,
Folmer James J.,
Werner Kim M.,
Weinreb Steven M.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000103)39:1<237::aid-anie237>3.0.co;2-b
Subject(s) - total synthesis , enantioselective synthesis , intramolecular force , chemistry , stereoselectivity , derivative (finance) , stereochemistry , ring (chemistry) , organic chemistry , combinatorial chemistry , catalysis , business , finance
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.