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Expedient Synthesis of (+)‐Lycopalhine A
Author(s) -
Williams Benjamin M.,
Trauner Dirk
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509602
Subject(s) - pyrrolidine , chemistry , moiety , aldol reaction , stereochemistry , total synthesis , intramolecular force , aldol condensation , mannich reaction , ring (chemistry) , bicyclic molecule , proline , enantioselective synthesis , amino acid , organic chemistry , catalysis , biochemistry
Two amino acids play a key role in the first total synthesis of lycopalhine A. l ‐glutamic acid serves as a convenient chiral starting material for the 13‐step synthesis, and l ‐proline promotes an unusual 5‐ endo ‐trig Mannich cyclization that generates the central pyrrolidine ring of the Lycopodium alkaloid. The bicyclo[3.3.0]octanol moiety of the molecule is formed through an intramolecular aldol addition that may occur spontaneously in nature.