SYNTHESIS OF RACEMIC, 2-(ALKYLTHIO)-6-(1-HYDROXYETHYL) PENEMS; ATTEMPTED PENEM SYNTHESIS VIA COPPER (I) - PROMOTED CYCLISATIONS

DOI: 10.1016/S0040-4039(01)81939-0

Source and publish data:

Tetrahedron Letters p. 3489 - 3492 (1981)

Update date:2022-08-06

Topics:

Authors:

McCombie, S. W.

Ganguly, A. K.

Girijavallabhan, V. M.

Jeffrey, P. D.

Lin, S. Lin, S.

at al. at al.

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Article abstract of DOI:10.1016/S0040-4039(01)81939-0

Stereocontrolled syntheses of the diastereoisomeric 6-(1-hydroxyethyl)-2-ethylthio and 2-(2-aminoethylthio)-penem-3-carboxylates from a common monocyclic azetidinone precursor are described.Cu (I)-promoted cyclisation of suitable N/C-3 secopenems is shown to yield "isopenems" (7-oxo-2-thia-1-azabicyclo<3.2.0>hept-3-enes) as the sole bicyclic product.

Full text of DOI:10.1016/S0040-4039(01)81939-0

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