An efficient asymmetric synthesis of the mercaptopyrrolidine side chain of an important β-methyl carbapenem antibiotic
An efficient asymmetric synthesis of the mercaptopyrrolidine side chain 2 1s described. The β-ketoester 4 is hydrogenated diastereoselectively to give the (R)-β-hydroxyester 5. The remaining functional groups are installed via a thiol Mitsunobu reaction and a reduction of a secondary amide to produc...
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Published in | Tetrahedron letters Vol. 38; no. 18; pp. 3203 - 3206 |
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Main Authors | , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
05.05.1997
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | An efficient asymmetric synthesis of the mercaptopyrrolidine side chain
2 1s described. The β-ketoester
4 is hydrogenated diastereoselectively to give the (R)-β-hydroxyester
5. The remaining functional groups are installed via a thiol Mitsunobu reaction and a reduction of a secondary amide to produce
2 in 34% overall yield from BOC-L-trans-4-hydroxyproline methylester
3 (Scheme 1).
The asymmetric synthesis of bis-HCl salt
2 of the thiol side chain of BO-2727 is described. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/S0040-4039(97)00613-8 |