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Synlett 2018; 29(08): 1117-1121
DOI: 10.1055/s-0037-1609303
DOI: 10.1055/s-0037-1609303
letter
Studies towards the Synthesis of the Antibiotic Tetrodecamycin
J.H. thanks the Clarendon Fund bursary, Oxford for financial support.Further Information
Publication History
Received: 28 December 2017
Accepted after revision: 19 January 2018
Publication Date:
16 March 2018 (online)


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.
Key words
Schlosser–Wittig reaction - intramolecular Diels–Alder reaction - aldol reaction - Dieckmann cyclization - tetronic acidSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609303.
- Supporting Information