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Total synthesis of (+)-negamycin and its 5-epi-derivative
- Source :
-
Tetrahedron . Jan2010, Vol. 66 Issue 1, p314-320. 7p. - Publication Year :
- 2010
-
Abstract
- Abstract: (+)-Negamycin was prepared in 13 steps in an overall yield of 31% from commercially available ethyl (R)-(+)-4-chloro-3-hydroxybutanoate. The key step in the reaction sequence was a highly stereoselective asymmetric Michael addition of chiral amine (−)-21 [(1S,2R)-(−)-2-methoxybornyl-10-benzylamine] into the α,β-unsaturated carbonyl moiety of key intermediate 8, thus establishing the second chiral center in (+)-negamycin. 5-epi-Negamycin was also prepared in a similar fashion. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 66
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 45638979
- Full Text :
- https://doi.org/10.1016/j.tet.2009.10.097