Synlett 2018; 29(08): 1117-1121
DOI: 10.1055/s-0037-1609303
letter
© Georg Thieme Verlag Stuttgart · New York

Studies towards the Synthesis of the Antibiotic Tetrodecamycin

Jing He
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK   Email: victor.lee@chem.ox.ac.uk
,
Jack E. Baldwin
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK   Email: victor.lee@chem.ox.ac.uk
,
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA, UK   Email: victor.lee@chem.ox.ac.uk
› Author Affiliations
J.H. thanks the Clarendon Fund bursary, Oxford for financial support.
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Publication History

Received: 28 December 2017

Accepted after revision: 19 January 2018

Publication Date:
16 March 2018 (online)


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Abstract

A study towards the natural product tetrodecamycin is reported. A modified Schlosser–Wittig reaction was utilized to prepare the precursor for the subsequent intramolecular Diels–Alder reaction, which delivered the trans-decalin ring of the natural product. The tetronic­ acid moiety of the molecule was prepared by a Dieckmann cyclization­. The cyclization of the tetronic acid to the trans-decalin double­ bond to form a seven-membered ring was examined.

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