Abstract
The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl Imine 2 to afford β-lactam 4. The same dianion reacted with N-ary1 imine 10 to give β-lactams 11, 12, and 13. A three-step sequence was used to convert 4 into the β-lactam-pyran hybrid 9 while a five-step sequence was developed to transform 11 and 12 into 9. Application of the carboxyinversion reaction to derivatives of 9 afforded protected analogs of the amino-saccharldes daunosamlne (5) and acosamine (6).
Original language | English |
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Pages (from-to) | 1283-1292 |
Number of pages | 10 |
Journal | Tetrahedron |
Volume | 45 |
Issue number | 5 |
DOIs | |
Publication status | Published - 1989 |
Externally published | Yes |
Bibliographical note
Copyright:Copyright 2014 Elsevier B.V., All rights reserved.
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry