A stereoselective synthesis of a 2-functionalized-methyl-1β-methylcarbapenem key intermediate via decarboxylation

Chemical Communications

Volumn , Issue 17, 1998, Pages 1817-1818

  Choi, Woo Baeg ^a   Lee, Jaemoon ^a   Lynch, Joseph E ^a   Volante, R P ^a   Reider, Paul J ^a   Reamer, Robert A ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; CARBAPENEM DERIVATIVE;

ARTICLE; DECARBOXYLATION; DRUG SYNTHESIS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY;

EID: 0032494090     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804125c     Document Type: Article

References (17)

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14. 1H NMR spectroscopy. The major isomer of 8 cleanly gave a >99:1 β:α mixture of 9, while the minor isomer of 8 gave the same 99:1 β:α mixture of 9 along with 7-10% ring opened by-product 4a.
15. During the desilylation, 7-10% of 4c was formed.
16. The C-l configuration was determined by conversion of 2a to the known acetate [ref. 3(a)]. The spectroscopic data of the acetate were found to be identical to those reported.
17. 3) 211.8, 168.5, 67.9, 65.3, 61.8, 51.4, 44.7, 25.8, 22.6, 17.9, 12.4, -4.3, -4.9.