We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Enantioselective Total Synthesis of (+)‐Incargranine A Enabled by Bifunctional Iminophosphorane and Iridium Catalysis.
- Authors
Miller, Anna A. M.; Biallas, Phillip; Shennan, Benjamin D. A.; Dixon, Darren J.
- Abstract
Herein we report the first enantioselective total synthesis of (+)‐incargranine A, in nine steps. The total synthesis was enabled by an enantioselective intramolecular organocatalysed desymmetrising Michael addition of a malonamate ester to a linked dienone substrate that established pivotal stereocentres with excellent enantio‐ and complete diastereoselectivity. Furthermore, a key hemiaminal intermediate was accessed by developing an iridium‐catalysed reductive cyclisation, and the scope of this transformation was explored to produce a range of bicyclic hemiaminal motifs. Once installed, the hemiaminal motif was used to initiate a biomimetic cascade to access the natural product directly in a single step.
- Subjects
IRIDIUM; CATALYSIS; ENANTIOSELECTIVE catalysis; NATURAL products; RING formation (Chemistry); BIOMIMETIC synthesis
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 2, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202314308