We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Organocatalytic, Asymmetric Total Synthesis of (−)-Haliclonin A.
- Authors
Guo, Lian‐Dong; Huang, Xiong‐Zhi; Luo, Shi‐Peng; Cao, Wen‐Sen; Ruan, Yuan‐Ping; Ye, Jian‐Liang; Huang, Pei‐Qiang
- Abstract
The first total synthesis of the alkaloid (−)-haliclonin A is reported. The asymmetric synthesis relied on a novel organocatalytic asymmetric conjugate addition of nitromethane with 3-alkenyl cyclohex-2-enone to set the stereochemistry of the all-carbon quaternary stereogenic center. The synthesis also features a Pd-promoted cyclization to form the 3-azabicyclo[3,3,1]nonane core, a SmI2-mediated intermolecular reductive coupling of enone with aldehyde to form the requisite secondary chiral alcohol, ring-closing alkene and alkyne metathesis reactions to build the two aza-macrocyclic ring systems, and an unprecedented direct transformation of enol into enone.
- Subjects
ORGANOCATALYSIS; CATALYSTS; CHEMICAL synthesis; DIAMIDES; STEREOCHEMISTRY
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 12, p4132
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201512005