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A novel approach to the synthesis of 2‐benzyl substituted pyrrolizidine and pyrrolizidinone ring systems
Author(s) -
ZhuJin Liu,
Liu C. T.,
RenRong Lu,
Feng Xu
Publication year - 1988
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19880060206
Subject(s) - pyrrolizidine , chemistry , ring (chemistry) , intramolecular force , olefin fiber , stereochemistry , organic chemistry , polymer
Abstract This paper reports a new method to the synthesis of 2‐benzyl substituted pyrrolizidinone and pyrrolizidine ring systems, which involves the use of a vinylogous N ‐acyliminium ion 12 as an initiator for the intramolecular olefin cyclization and subsequent rearrangement. The total syntheses of six unnatural new pyrrolizidinone and pyrrolizidine alkaloids 1, 2, 3, 4, 5 and 16 serve as examples.