Volume 18, Issue 24
Natural Products
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ChemInform Abstract: New Methylseleno-Promoted Ketene-Imine Cycloaddition Reaction. A Simplified Stereoselective Synthesis of Penam.

Y. NAGAO

Y. NAGAO

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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T. KUMAGAI

T. KUMAGAI

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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S. TAKAO

S. TAKAO

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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T. ABE

T. ABE

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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M. OCHIAI

M. OCHIAI

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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Y. INOUE

Y. INOUE

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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T. TAGA

T. TAGA

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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E. FUJITA

E. FUJITA

Inst. Chem. Res., Kyoto Univ., Uji, Kyoto 611, Japan

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First published: June 16, 1987

Abstract

The alkoxyketenes (I), formed in situ from the corresponding alkoxyacetyl chlorides and triethylamine, react with the methylselenothiazolines (II) to produce the methylselenopenams (IIIa) stereoselectively.

ChemInform Abstract

The alkoxyketenes (I), formed in situ from the corresponding alkoxyacetyl chlorides and triethylamine, react with the methylselenothiazolines (II) to produce the methylselenopenams (IIIa) stereoselectively. Reductive elimination of the seleno group yields the penams (IIIb). (Opt. rotations).

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