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Synthesis of Angularly Fused (Homo)triquinane-Type Hydantoins as Precursors of Bicyclic Prolines.
- Source :
- Synthesis; 2016, Vol. 48 Issue 3, p387-393, 7p
- Publication Year :
- 2016
-
Abstract
- An efficient strategy for a four-step synthesis of angularly fused tricyclic hydantoins as suitable precursors of cis-fused bicyclic a- amino acids is developed by combining a highly diastereoselective Bucherer- Bergs reaction of 2-alkenylcycloalkanones and a regiospecific selenium-induced closure of pyrrolidine ring. This methodology was applied in a five-step synthesis of bicycloproline derivatives in high overall yield. The method could be used for the multigram preparation of free conformationally constrained bicyclic a-amino acids with two points of diversity (size of cycloalkyl ring and substituent at the pyrrolidine ring). [ABSTRACT FROM AUTHOR]
- Subjects :
- QUINANES
HYDANTOIN
CHEMICAL precursors
PROLINE
REGIOSELECTIVITY (Chemistry)
Subjects
Details
- Language :
- English
- ISSN :
- 00397881
- Volume :
- 48
- Issue :
- 3
- Database :
- Complementary Index
- Journal :
- Synthesis
- Publication Type :
- Academic Journal
- Accession number :
- 112399006
- Full Text :
- https://doi.org/10.1055/s-0035-1561285