Antibiotic synthesis

Details Antibiotic synthesis Antibiotic synthesis

1992-06-12

1999-12-07

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540200, 540360, 540347, 540350, C07D 718, C07D20508, C07D50304, C07D49906

Patent

active

059986123

ABSTRACT:
A method of preparing intermediates for carbapenem antibiotics characterized by treating a N-deprotected acetoxy conpound of the formula: ##STR1## in the presence of a Lewis acid or a silylating agent to yeild an intermediate; and cyclizing the intermediate in the presence of rhodium (II) acetate to form a bicyclic ketoester.

REFERENCES:
patent: 4287123 (1981-09-01), Liu
patent: 4290947 (1981-09-01), Christensen
Karady, JACS 103, 6765(1981).
Oida, "Recent Advance in the Chemistry of Beta Lactam Antibiotics", p.330-348.
Reider, Tet. Letters 23, 379 (1982).
Chen, Tet. Letters 1977, p4183.
Paterson, Tet. Letters p 1519-1520 (1979).
Neetz I Chem Abs 95, 424465s,(1981).
Neetz II, Ang. Chem Int. Ed. 17, 48-9(1978).
Rasmussen, Synthesis 1977, p. 91.

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