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Synthesis of Bicyclic Proline Derivatives by the Aza‐Cope–Mannich Reaction: Formal Synthesis of (±)‐Acetylaranotin
Author(s) -
Belov Dmitry S.,
Ratmanova Nina K.,
Andreev Ivan A.,
Kurkin Alexander V.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405811
Subject(s) - bicyclic molecule , mannich reaction , formal synthesis , proline , chemistry , amino acid , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry
Herein we suggest an approach to oxygenated bicyclic amino acids based on an aza‐Cope–Mannich rearrangement. Seven distinct amino acid scaffolds analogous to the natural products were prepared on a gram scale with precise control of stereochemistry. Successful implementation of our strategy resulted in the formal synthesis of acetylaranotin.