Volume 18, Issue 38
Natural Products
Full Access

ChemInform Abstract: Chemistry of Penicillin Diazoketones. Part 2. From β-Lactam to β-Lactone.

H. LUDESCHER

H. LUDESCHER

Sandoz Forschungsinst., A-1235 Wien, Austria

Search for more papers by this author
C.-P. MAK

C.-P. MAK

Sandoz Forschungsinst., A-1235 Wien, Austria

Search for more papers by this author
G. SCHULZ

G. SCHULZ

Sandoz Forschungsinst., A-1235 Wien, Austria

Search for more papers by this author
H. FLIRI

H. FLIRI

Sandoz Forschungsinst., A-1235 Wien, Austria

Search for more papers by this author
First published: September 22, 1987

Abstract

The penicillanic acid methyl ester (I) is transformed into the diazoketone (II) which decomposes on treatment with catalytic amounts of rhodium(II) acetate to yield the β-lactone (III).

ChemInform Abstract

The penicillanic acid methyl ester (I) is transformed into the diazoketone (II) which decomposes on treatment with catalytic amounts of rhodium(II) acetate to yield the β-lactone (III). Photolysis of the diazoketone (IV) produces the β-lactone (V) which is cleaved by aniline (VI), forming the hydroxycarboxamide (VII). (Intermediates, mechanism).

    The full text of this article hosted at iucr.org is unavailable due to technical difficulties.