Open AccessTotal Synthesis of (±)-Impatien A via Aza-Heck Cyclization
Author(s) -
Katerina M. Korch,
Donald A. Watson
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c02767
Subject(s) - chemistry , total synthesis , heck reaction , alkene , natural product , electrophile , stereochemistry , ring (chemistry) , combinatorial chemistry , ligand (biochemistry) , nitrogen atom , radical cyclization , palladium , organic chemistry , catalysis , receptor , biochemistry
The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.