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Synlett 2020; 31(04): 378-382
DOI: 10.1055/s-0039-1691569
letter
© Georg Thieme Verlag Stuttgart · New York

Bicyclic Lactams Derived from Serine or Cysteine and 2-Methylpropanal

Halima Bagum
a   The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford. OX1 3TA, UK   Email: mark.moloney@chem.ox.ac.uk
,
Bethany R. Shire
a   The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford. OX1 3TA, UK   Email: mark.moloney@chem.ox.ac.uk
,
Kirsten E. Christensen
a   The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford. OX1 3TA, UK   Email: mark.moloney@chem.ox.ac.uk
,
Miroslav Genov
c   Oxford Antibiotic Group, The Oxford Science Park, Magdalen Centre, Oxford OX4 4GA, UK
,
Alexander Pretsch
c   Oxford Antibiotic Group, The Oxford Science Park, Magdalen Centre, Oxford OX4 4GA, UK
,
Dagmar Pretsch
c   Oxford Antibiotic Group, The Oxford Science Park, Magdalen Centre, Oxford OX4 4GA, UK
,
Mark G. Moloney∗
a   The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford. OX1 3TA, UK   Email: mark.moloney@chem.ox.ac.uk
b   Oxford Suzhou Centre for Advanced Research, Building A, 388 Ruo Shui Road, Suzhou Industrial Park, Jiangsu, 215123, P. R. of China
› Author AffiliationsH.B. gratefully acknowledges the award of a Scholarship from the Commonwealth Scholarship Commission.
Further Information

Publication History

Received: 05 December 2019

Accepted after revision: 27 December 2019

Publication Date:
21 January 2020 (online)

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Abstract

Bicyclic lactams may be prepared from serine or cysteine and 2-methylpropanal; the resulting S,N-heterocycles are more stable than the corresponding O,N-heterocycles but both are synthetic intermediates capable of further elaboration.

Key words

lactams - antibiotics - cyclisation - heterocycles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691569.
  • Supporting Information
 

  • References

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