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- Title
Atroposelective Total Synthesis of the Fourfold ortho‐Substituted Naphthyltetrahydroisoquinoline Biaryl O,N‐Dimethylhamatine.
- Authors
Slack, Eric D.; Seupel, Raina; Aue, Donald H.; Bringmann, Gerhard; Lipshutz, Bruce H.
- Abstract
A stereoselective total synthesis of O,N‐dimethylhamatine, an analogue of an axially chiral naphthylisoquinoline natural biaryl product from tropical Ancistrocladus lianas, is reported. The route features a late‐stage atropo‐diastereoselective biaryl bond formation. Generation of this especially challenging, sterically hindered tetra‐ortho‐substituted array was achieved by using Nolan's (IPr*NHC)PdCinCl pre‐catalyst under mild Negishi coupling conditions. Discussion is offered regarding the selectivity obtained experimentally and predicted from DFT calculations on the key biaryl coupling step that leads to the desired M‐diastereomer.
- Subjects
NATURAL products; LIANAS
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 62, p14237
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201903832