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Proline Derived Bicyclic Derivatives through Metal Catalysed Cyclisations of Allenes: Synthesis of Longamide B, Stylisine D and their Derivatives
Author(s) -
Jovanovic Milos,
Petkovic Milos,
Jovanovic Predrag,
Simic Milena,
Tasic Gordana,
Eric Slavica,
Savic Vladimir
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901554
Subject(s) - bicyclic molecule , chemistry , allene , catalysis , proline , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , amino acid , biochemistry
Annulations of allene‐substituted proline derivatives promoted by transition metals have been investigated as a general way to access bicyclic structures with a bridgehead nitrogen. Two processes, Pd‐ and Ag‐catalysed cyclisations, have been employed complementary to control the substitution pattern of the product. The investigated methodologies afforded the bicyclic derivatives in comparable yields, while Ag‐catalysis showed higher level of diastereoselectivity. Both processes have been utilized in the synthesis of naturally occurring pyrroles longamide B, stylisine D and their derivatives.