Synthesis of Cyclosiphonodictyol A and Its Bis(sulfato)
Juan A Gil1, Fabio Arias1, Rachid Chahboun1
1Departamento de Quı́mica Orgánica, Facultad de Ciencias, Instituto de Biotecnologı́a, Universidad de Granada, 18071 Granada, Spain.
Abstract:
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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