Spirocyclic Penicillins

DOI: 10.1039/P19870000635

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 635 - 638 (1987)

Update date:2022-09-26

Topics:

Authors:

Burton, George

Harrington, Frank P.

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Article abstract of DOI:10.1039/P19870000635

The intramolecular, mercury-mediated cyclisation of (6S)-benzyl 6-<(R)-and (S)-2-amino-2-phenylacetamido>-6-(methylthio)penicillinates, (8) and (9), has been shown to give spiro derivatives.Unexpectedly, products (16) and (17), derived from attack on the more-hindered β-face, were isolated in addition to the predicted products (10) and (11), formed by attack on the α-face.Formylation and removal of the carboxy protecting group gave spirocyclic penicillins devoid of useful antibacterial activity.

Full text of DOI:10.1039/P19870000635

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