Journal
SYNLETT
Volume -, Issue 19, Pages 2845-2849Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0032-1317491
Keywords
aldol reactions; selectivity; natural products; hydroquinone; total synthesis
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A ring-closing metathesis (RCM) approach was envisioned for installing the E double bond at the C9 and C10 positions of divergolide A, isolated from a mangrove endophyte. Accordingly, the C10-C15 diene diol fragment and the amido hydroquinone core with the requisite functionalities and stereochemistry have been synthesized by using the norephedrine-based syn-selective glycolate aldol and the anti-selective aldol reactions, respectively. CuI-catalyzed amidation was employed to access the anilide intermediate, which was further transformed into the amido hydroquinone core.
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