Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 5, Pages 3799-3805Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03434
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Funding
- Spanish Ministry of Economy and Competitiveness [CTQ2014-56611-R/BQU]
- Regional Government of Andalucia [P11-CTS-7651]
- Spanish Ministry of Education, Culture and Sports
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The first synthesis of the marine benzoxepane hydroquinone cyclosiphonodictyol A and its bis(sulfato) from commercial (+)-sclareolide is reported. The key steps of the synthetic sequence (11 steps, 46% global) are the nucleophilic attack of a hindered tertiary alkoxide, a ring-closing metathesis reaction, and the Diels-Alder cycloaddition of a dienol acetate.
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